Commentary: The Journey and Future of (2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate

Historical Development

Researchers have always looked for new twists on nucleoside analogs to stay one step ahead in pharma and diagnostics. Back in the late 20th century, chemists chasing better antiviral therapies turned their eyes toward the modifications of cytidine backbones. Once scientists figured out how to introduce fluorine and methyl groups at the 2-position of cytidine, it opened the door to all sorts of activity tweaks: the analog’s resistance to enzymatic breakdown, its tighter or looser fit with viral polymerases, and finer control over toxicity. The benzoylation on both the 3’ and 5’-hydroxyl groups and an N-benzoyl group further adjusted the molecule’s profile, making it an intriguing candidate not only for chemical stability but also for docking into DNA and RNA chains when studying polymerase reactions. What began as a curiosity in labs quickly became an important scaffold for research, feeding into a feedback loop between synthetic chemistry and molecular biology.

Product Overview

(2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate offers a fine balance—designer nucleoside analogs don’t come cheap, but they open unique doors for researchers and industry. Tracing the supply chain back to the synthesis bench, you won’t find this compound by accident—each modification stacks to deliver specific properties. Whether a team pursues antiviral leads, works on next-gen sequencing platforms, or seeks new chemical probes for DNA polymerases, this analog serves as an essential stepping stone. Its carefully crafted structure allows for insight into enzyme mechanisms, substrate specificity, and resistance development at the biochemical level.

Physical & Chemical Properties

As a solid, (2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate typically crystallizes in a stable, off-white form, not prone to degrading at room temperature as long as it’s kept dry and out of direct sunlight. With molecular weight stacking above 600 Da and a fairly bulky aromatic protection out on the sugar’s ends, this compound doesn’t dissolve in water, leaning toward polar aprotic solvents like DMSO or DMF. The fluorine swapping at the 2’ spot really shows up in its 1H and 19F NMR signatures, helping lab staff check purity and structure. HPLC and mass spectrometry provide quality controls, and it’s no secret that its melting point sits higher than its unprotected forerunner, making it more robust in certain synthesis chains.

Technical Specifications & Labeling

Every properly labeled vial comes with a certificate showing purity, batch number, date of manufacture, recommended storage temp, and precautionary hazard codes. Synthetic nucleoside suppliers know that researchers can’t afford surprises in the lab—each lot’s consistency matters. Standard reference spectra (NMR, MS, elemental analysis) go out with shipments, and researchers expect the label to make all stereochemistry and protecting groups obvious. It’s common to highlight sensitive handling requirements—this isn’t a kitchen staple. Storage in a dry, inert environment at 2–8°C preserves stability, and careful logging prevents confusion during critical experiments.

Preparation Method

Producing (2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate takes more than basic organic chemistry. Starting from a protected cytidine backbone, careful fluorination and methylation at the 2-position typically use fluorinating agents like DAST or Deoxo-Fluor, under tight conditions to avoid over-reactions or racemization. The N-benzoylation comes next, with benzoyl chloride and a base, and workers carry out the final benzoylation at the 3’ and 5’ hydroxyls. Several rounds of purification, usually flash chromatography and crystallization, yield the final product. Quality control here makes or breaks the prep—a failed fluorination means wasted materials, and impurities mess up bioassays.

Chemical Reactions & Modifications

Once it lands in a chemistry lab, the analog serves as a gateway for further modifications. Researchers can cleave the protecting groups to free up the nucleoside for incorporation into oligonucleotides. Enzymologists might use it in polymerase reactions, observing how the combination of fluoro and methyl tweaks stacking interactions and hydrogen bonding. Some teams build prodrugs using the protected analog as a starting point, attaching linkers tailored for enzymatic release inside cells. Reactions involving phosphorus chemistry bring it into play as a building block for novel nucleic acid analogs, positioning this compound as more than just a finished product—it’s a campfire for new ideas in nucleotide chemistry.

Synonyms & Product Names

As with many specialty reagents, the same compound wears different hats. Common synonyms in catalogs include “Bz-F-Me-Cytidine dibenzoate,” “2-Deoxy-2-fluoro-2-methylcytidine dibenzoate,” or “N-Benzoyl-F-Me-dC 3’,5’-dibenz.” In publications and patents, the shorthand often drops to “F-Me-dC(Bz)(Bz),” with stereochemistry assumed clear in context. This patchwork of aliases sometimes sows confusion, especially for newcomers—careful cross-checking between vendor specs and literature saves time.

Safety & Operational Standards

Handling this analog needs respect for standard chemical safety rules, plus a few extra steps for nucleoside reagents. Eye protection, gloves, and fume hoods aren’t optional; splashes from benzoyl chlorides or fluoro reagents pose real risks. Dust or powder spills can cause respiratory irritation, and trace benzoyl groups act as allergens for some people. Labs document safety data sheets, align with GHS guidelines, and run internal safety briefings. Waste disposal doesn’t end up down the drain—dedicated solvent bins and incineration pick up where the synthesis ends. Training on emergency protocols, spill containment, and chemical inventory is mandatory—labs that cut corners can end up in the news for all the wrong reasons.

Application Area

Researchers increasingly depend on nucleoside analogs for molecular biology, pharmaceuticals, diagnostics, and biochemical assays. This compound plays a direct role in studying how polymerases deal with modified nucleotides—a hot topic in both drug resistance and next-generation sequencing. Its resilience to enzymatic cleavage, combined with easy deprotection, makes it essential in antisense oligonucleotide research and DNA-based therapeutics. In pharma, analogs like this one show up in screens for new antivirals, especially against viruses that develop resistance to older drugs. The compound’s uniqueness allows it to slip by certain viral enzymes while tripping up others—true for hepatitis, herpes, and other hard-to-target pathogens. Academic groups and industrial labs continue to push its use in DNA/RNA probe design, hoping to unlock faster, cheaper, and more accurate diagnostic tests.

Research & Development

Partnering between academia and industry drives much of the innovation around this analog. Structural biologists use it to chart crystal structures of polymerase-substrate complexes, mapping the delicate dance between hydrogen bonds, stacking forces, and active site geometry. Medicinal chemists screen closely related analogs, swapping out benzoyl groups, tweaking sugar configurations, or adjusting electronic properties to search for better drug leads. Startups pitching breakthroughs in precision medicine often mention these protected nucleosides in patent filings, betting on their chemical uniqueness for market exclusivity. Funding agencies are putting more trust in collaborative research, so cross-disciplinary teams get together—synthetic chemists, computational modelers, and cell biologists share data and insights to leapfrog traditional development timelines.

Toxicity Research

Every new analog faces uphill battles in toxicity studies. Researchers start with in vitro enzyme assays, then graduate to cellular models—looking for off-target effects, breakdown products, or evidence of DNA damage pathways getting activated. These studies often uncover subtle risks: a well-shielded analog might sail through human polymerases but slip past DNA repair machinery, or generate metabolites that hit cellular red flags. Animal studies and detailed ADME (Absorption, Distribution, Metabolism, Excretion) profiling follow, with teams watching for kidney or liver accumulation, blood-brain barrier crossing, and long-term mutagenicity. In my own experience, transparency matters—there’s no shortcut in reporting adverse findings, and peer review weeds out wishful thinking. All this diligence pays off when one of these analogs gets the nod for further drug development or a large-scale diagnostic rollout.

Future Prospects

Interest in modified nucleosides continues to surge. With more infectious disease threats, antibiotic resistance, and precision gene editing around the corner, analogs like (2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate aren’t just shelf items but part of bigger solutions. As more is learned about enzyme selectivity, molecular modeling improves, and automated synthesis platforms scale up, expect the cost and complexity of these analogs to come down. Synthetic biology could use these molecules in designer genomes or programmable circuits, while pharma sharpens its focus on safer antivirals and gene-editing tools. Training and safety standards need to keep pace; global collaboration ensures new findings don’t stay siloed. My take on it: this analog represents both a benchmark for chemical ingenuity and a reminder that every good reagent stands on decades of careful research, tough choices about safety, and the real-world drive to solve urgent biological problems.



What is the chemical structure and formula of (2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate?

Stepping into the World of Modified Nucleosides

Deep in the world of chemical biology, small tweaks to a molecule can make remarkable differences in how our medicines work. Chemists love a challenge, and designing (2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate presents one worth talking about. Even the name hints at the number of adjustments baked in by expert hands: a cytidine base that’s been benzoated, fluorinated, methylated, and stripped of a hydroxyl or two.

The Shape of Innovation

One core reason this molecule matters shows up in its skeleton. Chemically, the backbone is rooted in cytidine, a nucleoside with a ribose sugar linked to a cytosine base. Here, the 2-position swaps one hydrogen for a methyl and another for fluorine—tiny changes that pack a punch in how the nucleoside interacts in biochemical systems.

Protective benzoyl groups at the 3’ and 5’ positions shield the molecule. I remember sitting in a lab as an undergrad, watching my own mentor explain why we throw these bulky groups on sugars or nucleosides. They don’t just protect reactive spots during synthesis—they also nudge solubility and stability, making purification a little less of a headache. The N-benzoyl group on the cytosine ring gives one more layer of protection and tweaks electronic properties, helping the molecule slip into chemical reactions with more control. Chemists call these moves “orthogonal protection”—a term that felt fancy to me until I actually struggled to deprotect one group without ruining the rest of the molecule.

Chemical Details That Matter

The formula for this specific compound spells out just how much has been added: C34H29FN4O6. Counting carbons, hydrogens, fluorine, nitrogens, and oxygens adds up to a structure that’s big for a nucleoside analog. Chemically, it looks like this:

Chemical formula: C34H29FN4O6Key functional features:

  • A cytidine core, deoxy at the 2’ position, which now holds a fluorine and a methyl group
  • Benzoyl esters decorating both the 3’ and 5’ hydroxyls of the sugar ring
  • A benzoyl group on the exocyclic amine of the cytosine base

The Bigger Picture for Research and Medicine

Why go to so much trouble? Compounds like this one emerge in research chasing better analogues for medicine—think antiviral drugs, especially those aimed at viral polymerases, or as building blocks for synthetic RNA research. One faulty methyl or missing protection group in synthesis can lead to inactive, or even toxic, end products. Fluorine brings in stability, often making molecules harder for enzymes to chop up. Methyl groups can nudge base pairing and change how a drug fits in a pocket. The exact arrangement of these extras also lets researchers craft prodrugs with precise properties.

Challenges come from making them pure and analytically robust. Pinpointing each modification, confirming by NMR, mass spectrometry, and chromatography, becomes tedious but necessary. From my own projects working with similar protected nucleosides, I’ve learned a failed protection or quirk in purification can eat up weeks, not hours. Bringing together organic chemistry’s toolkit and a dose of patience turns a convoluted string of atoms into a molecule that might form the basis of tomorrow’s medicines.

What Moves Us Forward

It’s easy to get lost in the detail. Each tweak to a molecule like (2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3’,5’-dibenzoate points to the bigger aim: making better, more reliable tools for targeting disease at its foundation. Solutions involve better protecting groups that install and leave cleanly, analytical methods that speed up troubleshooting, and collaborative science that crosses chemistry and biology. Only with careful attention to every atom and every step do we arrive at the kinds of advances that push medicine ahead.

What are the main applications or uses of this compound?

The Role of Sodium Bicarbonate in Healthcare

Sodium bicarbonate often goes by “baking soda,” and many households keep it handy. In healthcare, it does a lot more than just settle an upset stomach. Doctors use it to treat certain types of acidosis, a condition where the body produces too much acid or the kidneys cannot remove enough acid. Even in emergency rooms, medical staff reach for sodium bicarbonate when treating some overdoses, especially those involving certain drugs that make the blood dangerously acidic.

Dentists recommend toothpaste containing this compound for its ability to neutralize plaque acids. Researchers have studied sodium bicarbonate for its potential to help with chronic kidney disease as it can reduce acid buildup in the bloodstream. The science behind it is more than tradition; its track record in hospitals and clinics makes it a trusted tool in medicine cabinets around the world.

Sodium Bicarbonate in Food Preparation

Walk into any bakery, and odds are, sodium bicarbonate is in reach. Bakers rely on it because it acts as a leavening agent. By reacting with acidic ingredients, it forms carbon dioxide, causing dough or batter to rise. The chemical reaction creates the light, fluffy texture many people like in cakes, pancakes, and cookies.

Commercial food producers also use this compound for tasks like balancing pH or softening vegetables. It keeps color and texture in canned vegetables, and it makes pre-cooked beans tender—all without strong flavors.

Cleaning, Deodorizing, and Personal Care

Few cleaning products work on as many surfaces as sodium bicarbonate. Scrubbing with it cleans stovetops, tubs, and sinks with very little effort. Unlike harsh cleansers, it doesn’t scratch, making it safe for most finishes. I use it to soak coffee mugs stained with tannins. It loosens residue so you don’t need to scrape.

This compound tackles odor, too. Fridges and shoes often trap smells, but an open box of baking soda absorbs these well. Science supports this—it reacts with both acidic and basic odor molecules to neutralize them. Many deodorants use a sprinkle of sodium bicarbonate because of this quality. People with sensitive skin find baking soda an inexpensive alternative to name-brand deodorants.

Industrial and Environmental Uses

Factories use sodium bicarbonate for more than recipes. It works in fire extinguishers, especially the dry chemical type for grease or electrical fires. Mixing powdered sodium bicarbonate in extinguishers causes it to release carbon dioxide that smothers flames.

Municipal water treatment plants depend on this compound to balance water pH. Keeping the right acidity matters for pipes and public health. Environmental agencies also use sodium bicarbonate to treat acid spills. In power plants, sodium bicarbonate controls sulfur dioxide emissions, helping reduce air pollution.

Potential Solutions and Considerations

Not every use causes excitement. Some concerns involve environmental impact from large-scale mining and manufacturing. Choosing sodium bicarbonate sourced from sustainable operations—like those using naturally occurring trona ore—can cut down on resource waste. At home, simple steps like storing baking soda correctly extend its shelf life and reduce waste. Industries that recycle their spent material also play a part in lowering chemical waste.

By understanding both its benefits and the need to use it wisely, each of us helps keep sodium bicarbonate working safely in medicine, food, daily life, and the environment.

What is the recommended storage condition for (2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate?

Learning From the Lab: Realities of Handling Compounds

A lot of folks outside research circles don’t see the hours lost to little oversights like temperature swings or missed light exposure warnings. Anyone who has prepped nucleoside analogues—let alone tricky ones with a benzoyl group and sensitive fluorine—learns quickly that careful storage means the difference between reliable results and piles of wasted time. Pulling the wrong vial from an ambient shelf, even for one afternoon, can ruin a run. Personal frustration aside, the financial hit stings. Watching a compound degrade after weeks of synthesis never fades from memory, and it drives home the impact of proper storage.

Deep Freeze Isn’t Just Overkill—It’s Standard

Standard guidance recommends keeping such nucleoside analogues in a freezer, ideally at –20°C. That’s not just about being overcautious. Studies from journals like Bioorganic & Medicinal Chemistry repeatedly point to thermal instability in modified cytidine derivatives. Even minor temperature rises can trigger hydrolysis or slow decomposition, reducing yield and reliability. Lab groups have published countless examples where shelf life drops from months to days when bench temperatures go above freezing.

No Mixed Messages: Keep It Dry, Keep It Dark

Moisture plays a huge role. Benzoyl esters, while handy for protecting active groups during synthesis, come with their own set of risks. Water in the air can sneak into poorly sealed vials, gradually knocking off those benzoyl groups and converting a pure product into a stubborn mess. Dry air, desiccant packs, and screw-top vials with decent seals matter. Skipping these steps almost always means headaches later when the expected melting point or NMR spectrum drifts out of spec.

Light presents another risk. Plenty of fluorinated nucleoside analogues break down under fluorescence or even ordinary room lighting, which hops electrons around unstable molecular centers. A quick check in the dark room with a UV lamp often reveals photobleaching. Dark storage—think foil-wrapped vials tucked in a closed box inside the freezer—gives a simple, cost-effective solution.

Label Like It Matters—Because It Does

Compounds with long fancy names stand in a freezer for months, sometimes years. Clear labeling with preparation date, concentration, and known storage requirements isn’t just a formality. Old habits die hard, and sharpie-faded glass vials have misled too many careful scientists. The memory of trying to piece together a failed experiment, only to spot a “room temperature” label on a delicate reagent, sticks. Lab management manuals push for digital inventory these days, and the convenience shows when tracking stability or tracing failures.

Simple Steps for Every Researcher

Once frozen, sealed, and labeled, the next best move involves minimal disturbance. Routine inventory checks limit unnecessary thawing, which prevents temperature cycling that can mess with purity. Retrieval should be quick, returning unused compound to the cold as soon as possible. Even the cleanest labs slip into bad habits if these routines aren’t reinforced—senior scientists set a tone by insisting every vial lands back in the right place, not left out to “warm up” on a crowded benchtop.

Making storage precautions second nature ultimately protects breakthroughs and budgets. Without exaggeration, proper handling often marks the dividing line between a landmark result and a string of avoidable questions at the next group meeting.

Is this product available in different purity grades or quantities?

Understanding Product Choices

When buying chemicals or materials, the first question that pops up is: can I get it in different purity grades or quantities? It's not just curiosity or convenience—this matters for real reasons. As someone who’s worked in both teaching labs and small businesses, these options have a direct impact on safety, project costs, and outcomes.

Differing Needs, Real World Scenarios

A research lab doesn’t have the same requirements as a soap-making entrepreneur down the street. A chemistry professor who teaches undergraduates only needs small bottles—nothing that breaks the bank, just enough for a few experiments. On the other hand, a business scaling up production wants larger quantities at a decent price, but they might not need the “ultra-high” grade a scientific researcher demands. This is where choices in quantity and purity actually make a difference. Getting stuck with industrial-size drums or only pharmaceutical-grade options drives up costs or complicates storage, with a higher risk of waste.

Why Purity Levels Affect More Than Performance

Purity isn’t just about technical bragging rights. It affects results and sometimes, lives. Food manufacturers rely on food-grade inputs. A slightly impure product might make no difference to a cleaning solution but could throw off results in a DNA lab or put people at risk in pharmaceuticals. In agriculture, crop treatments must hit a specific standard so farmers don’t risk safety or their harvest. No one wants to guess if their fertilizer or medicine meets the right threshold.

Price and Accessibility

Shopping for materials, price tends to be linked to both purity and quantity. Purchasing a ton of something at technical grade often costs less than a kilogram of reagent grade product. This isn’t just mark-up for the sake of it. Purity takes extra work—removing contaminants, testing, and documentation all cost money. For cash-strapped schools or DIYers, flexibility in purity and package size is the difference between being able to experiment or walking away.

Consistency and Trust

People rely on brands and suppliers who publish transparent specs for both purity and quantity. Having good documentation builds trust. I always look for certifications and analysis reports. Transparency helps users make informed choices. Lack of options—one grade, one size—drives folks to unfamiliar sources or black-market suppliers, which poses health and quality risks. A strong, well-backed supply chain erases so much uncertainty for labs and businesses alike.

How to See Solutions Moving Forward

Suppliers with flexible packaging, multiple purity grades, and clear labelling lower the barriers for new ideas and safer use. Companies benefit if they listen to user feedback—one product doesn’t fit all. Regulatory agencies and industry leaders should push for more standardized documentation and accessible options. Local distributors can play a bigger role, helping bridge between manufacturers and end-users with advice on what fits a specific project or budget.

Variety in grades and quantities does more than pad catalogues. It makes innovation possible. It helps small players enter the market. Every person—whether a scientist, student, or entrepreneur—deserves to buy what fits their needs, not just what’s convenient for big suppliers.

What are the safety and handling precautions for this compound?

Paying Attention to Safety for Compound Handling

If you’ve ever worked with chemicals, you already know that a lax attitude leads to trouble. Whether in a basement lab or a factory, the risks look the same: chemical burns, respiratory harm, fire, and sometimes outcomes nobody likes to talk about. People can get casual after a while. Gloves slip off, a mask feels uncomfortable, or someone skips reading a label because routine breeds confidence. That’s where problems start. For any chemical, it pays to stop and ask: what’s in front of me, and what could go wrong?

Understanding Real Risks, Not Just the Label

Labels tell part of the story. Safety Data Sheets fill in gaps, spelling out hazards like flammability, reactivity, or toxicity. A pinch of a caustic powder, fumes from volatile solvents, or a splash of strong acid all demand respect. I remember a day in the lab—forgot to clamp a hose on a distillation and ended up needing the eyewash station. The solution always starts with protective gear. Nitrile or rubber gloves block acids and bases. Goggles protect your eyesight. A lab coat keeps sleeves and skin from getting that accidental splash. Closed shoes avert drips from burning skin straight through socks. The best solution: just dress like a slow-moving knight, every time, no excuses.

Keep It Contained and Clean

Spills aren’t rare. You get distracted, a flask tips, the contents spread faster than you can react. This is why containment pans matter. I’ve watched people try to grab chemicals with bare hands instead of using a scoop or tweezers. Not smart. Work tidy. Return lids. Wipe up spills the right way—with absorbent pads and proper neutralizers, not a handful of paper towels. Dispose of used towels and gloves in the right bins. One person dumping solvent-soaked cloths into the regular trash brings everyone’s safety into question. It doesn’t just look bad; it gives regulatory authorities a reason to step in.

Air Matters

Some chemicals release invisible vapors that catch up with workers later. Keep operations involving strong fumes or powders under a fume hood. A well-maintained hood draws away hazards. Ignore the urge to “just do it quickly.” I’ve seen dozens of cases where a shortcut led to headaches, dizziness, or worse.

Fire Hazards and Storage Sense

Flammable materials and oxidizers belong far apart. Solvents stored near open flames or hot plates invite disaster. I’ve learned to double-check labels before mixing anything; some chemicals react violently with water, others spark if mixed incorrectly. Store acids, bases, and organics in separated, clearly labeled cabinets, and make sure lids close tight. Routine monthly checks help catch broken seals or expanding containers before leaks happen.

Training Makes the Difference

Most injuries could be stopped with better training. Each year, I run into folks who have handled dangerous materials for decades but skip refreshing their skills. Refresher courses keep safety on people’s minds and remind everyone how fast things can go wrong. No shame in pausing to ask questions—seasoned pros and beginners alike.

The right approach isn’t about paranoia. It’s grounded in knowing one mistake can undo years of safe practices. Trusting routines doesn’t cost anything, but ignoring them does. Pay respect to the hazards, keep the workspace tight, suit up, and treat every session with chemicals like it’s your first time. Common sense, perhaps, but that’s what keeps the lab and the people in it healthy.

(2R)-N-Benzoyl-2-deoxy-2-fluoro-2-methylcytidine 3',5'-dibenzoate