Methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate: An In-Depth Commentary

Historical Development

Chemical syntheses have always pushed boundaries. Chemists in the late twentieth century grew curious about stabilizing intermediates and targeting specific enantioselective products. This curiosity drove people to experiment with new molecular protection tactics. The tert-butyldimethylsilyl (TBDMS) group gained traction as an efficient protecting group for alcohols due to its robust stability under various conditions. The continuous refinement of Wittig chemistry also interested researchers for carbon-carbon bond formation. By the time methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate appeared in scholarly papers, most core technologies for its assembly were already tried and trusted in pharmaceutical and synthetic laboratories. The molecule arose as an answer to the demand for more reliable intermediates in complex organic synthesis—especially where stereo and regioselectivity shape the research outcome.

Product Overview

This molecule blends the rigor of protecting group strategies with the power of phosphorus ylides. By choosing the methyl ester backbone and functionalizing it at multiple locations, chemists gain control over reactivity in their sequence of transformations. Its design provides clear advantages in both storage and handling. It stands as a sturdy intermediate. Researchers needing flexible building blocks recognize this compound as no-nonsense; it often steps in when robust selectivity is non-negotiable, especially for the total synthesis of structurally complex bioactive compounds.

Physical & Chemical Properties

The structure boasts a pale yellow to colorless appearance in purified form. Solubility favors organic solvents such as dichloromethane or chloroform more than aqueous systems. It usually arrives as an oil or crystalline solid, depending on minor impurities or conditions during isolation. Odor remains faint and unremarkable compared to basic esters. Thermal stability holds up to modest heating, with degradation above 100°C and hydrolysis risks at extremes of pH. Reactions favor mild conditions to safeguard the oxo and silyl groups from decomposition. Its NMR shows typical signals: broad shielded tert-butyl singlet, dimethylsilyl peaks, and aromatic proton resonances from the triphenylphosphoranyl group—these resonate as strong identifying features during quality checks.

Technical Specifications & Labeling

Labels need to indicate chemical purity (usually over 95%), specific rotation to confirm stereochemistry, and storage recommendations to avoid moisture contact. Labels note the compound’s full IUPAC name for clarity. Suppliers often mention glass container preference. Handling recommendations urge gloves and goggles, reflecting its sensitivity towards acids and bases, and its capacity to irritate skin and eyes. Batch numbers tie back to chromatograph purity records available on request, which remains crucial for reproducibility in research settings. The presence of phosphorus and silicon demands a precise note on hazardous waste management on material safety data sheets.

Preparation Method

Synthesis usually starts by protecting a chiral hydroxy ester with TBDMS chloride in the presence of imidazole, forming the silyl ether. The subsequent introduction of a phosphonium ylide—crafted from triphenylphosphine and an appropriate alkyl halide—lets chemists apply the famous Wittig reaction, which partners carbon frameworks in one efficient step. Oxidation or reduction steps fine-tune the ketone or hydroxy positions. The process rarely happens as a single-pot transformation due to incompatibility between strong bases and the protecting group. Routinely, chromatographic purification follows to remove triphenylphosphine oxide, a stubborn byproduct. Dry conditions are mandatory throughout, as silyl ethers reverse to parent alcohols under trace acid or water exposure.

Chemical Reactions & Modifications

The core features of the molecule make it versatile for downstream transformations. The tert-butyldimethylsilyl group remains steadfast during most oxidations or reductions, letting researchers selectively target other functionality. The phosphoranyl ylide allows further elongation or cyclization by transition-metal catalysis or classical ionic pathways. Removal of the silyl group at the final step—using tetra-n-butylammonium fluoride (TBAF) or mild acid—exposes the free alcohol for further modification. This routine fits especially well in total syntheses where late-stage deprotection opens gates to key intermediates without risking upstream sensitive groups.

Synonyms & Product Names

Synonyms reflect the breadth of its use. Besides its systematic IUPAC moniker, chemists call it by shorthand descriptors like "TBDMS-protected hexanoate ylide" or reference supplier catalog numbers. The name "triphenylphosphoranylidene hexanoate" also circulates in patent literature. Consistency in naming is key when ordering or cross-referencing papers, especially for less experienced lab personnel.

Safety & Operational Standards

Safe handling of this compound draws on lessons from years of organic experimentation. Wearing nitrile gloves, lab coats, and protective eyewear is standard practice. Its phosphorus content can cause irritation or react with oxidizing agents; the silyl ether part breaks down into volatile silanols under harsh conditions, prompting good ventilation. Work in a well-functioning fume hood—limiting exposure and protecting sensitive reactions from moisture in the air. Disposal follows hazardous waste protocols, especially for phosphorus byproducts. Ingesting or prolonged skin contact draws an immediate trip to the safety shower or medical attention.

Application Area

Researchers value this molecule in multi-step organic syntheses leading toward biologically active natural products or pharmaceutical candidates. Medicinal chemists benefit where stereoselectivity, protection, or deprotection cycles affect the final product profile—especially for enzyme inhibitors and small molecule drugs. Synthetic methodologists cite its role in validating new reaction conditions or catalytic transformations. Industrial chemists rely on such protected intermediates when scaling up laboratory protocols without risking costly decomposition or contamination from unprotected alcohols.

Research & Development

Lab groups experimenting with innovative catalysts often choose this compound to probe selectivity and compatibility. It helps troubleshoot new ligand designs or process optimizations in Wittig or Julia-Kocienski coupling routes. Pharmaceutical teams testing new synthesis routes for active ingredients find that the compound’s stability sidesteps bottlenecks tied to hydrolysis-prone intermediates. The structure also serves as a test bed for machine learning predictions in organic synthesis, making it a staple in both hands-on and informatics-driven research environments.

Toxicity Research

Data on toxicity remains limited, as the molecule’s complexity means it rarely appears outside controlled labs. In in vitro assessments using human and animal cell cultures, the silyl ether and triphenylphosphine fragments display low acute toxicity but call for caution due to their potential breakdown products. Prolonged exposure studies highlight mild irritation. Each new derivative or batch warrants re-testing, particularly in drug development where metabolic pathways and clearance rates become more significant. Modern labs log all exposure incidents, as regulatory standards tighten on organophosphorus compounds.

Future Prospects

Chemists consistently demand reliable intermediates as total synthesis projects grow more challenging and as drug candidates rise in complexity. Methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate offers a template that could influence automated synthesis strategies and module-based chemical factories of the future. Improvements in deprotection chemistry and waste minimization remain on the agenda. Newer detection and purification methods might broaden its utility, especially with more green and sustainable approaches. As data-driven chemistry joins hands with experimental know-how, this molecule’s adaptability could open even more doors for next-generation pharmaceuticals and specialty chemicals.



What is the chemical use of Methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate?

Getting to Know This Unique Molecule

Methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate is a mouthful, yet its importance in modern synthetic chemistry can’t be overstated. Years back, in a small organic lab tucked away in a university basement, I watched graduate students wrangling with this compound. Not for show, but because its structure makes it a strong ally during the synthesis of more complicated molecules, especially in medicinal chemistry.

Building Blocks and Strategic Reactions

One clear reason this compound attracts attention lies in its functional groups. The tert-butyldimethylsilyl (TBS) protecting group shields the oxygen, keeping reactive hands away while sensitive work takes place. With the TBS group on, chemists direct reactions precisely, reducing the odds of damaging the molecule. Silyl-protected alcohols, like this one, have revolutionized the art of chemoselectivity and brought speed to once slow steps. In personal experience, nothing slows progress like constantly backtracking to protect a reactive site, and compounds like this address that concern head-on.

Triphenylphosphoranylidene hints at the Wittig reaction, which is a tool every organic chemist either loves or dreads, depending on the day. This ylidenyl portion lets the molecule serve as a Wittig reagent precursor, and that opens doors to creating new carbon-carbon double bonds—vital for constructing complex natural products, especially those with double-bonded carbon skeletons like steroids or certain antibiotics. After seeing candidates rise and fall in drug discovery, it’s clear that shortcutting even a single step with well-designed intermediates can save time and resources.

Real-World Connections: Pharmaceuticals and Beyond

The pharmaceutical world depends on molecules like this to deliver medicines faster, cheaper, and with fewer hitches. Many blockbuster drugs are built molecule by molecule in painstaking sequence. With the TBS group protecting hydroxy sites, and the Wittig fragment ready for bond formation, chemists assemble key fragments that form the backbones of antiviral agents, statins, or anti-cancer compounds. For me, watching the transition of these specialty chemicals from sketchbooks to approved medication has always underscored how much starts at the bench, long before a product lands on a pharmacy shelf.

Challenges and Safer Chemistry

No chemical comes free of baggage. Specialty reagents mean waste streams, careful handling, and strict ventilation. Tert-butyldimethylsilyl compounds, for example, sometimes generate by-products that persist in the environment. Phosphorus-containing wastes, if not controlled, can harm aquatic systems. The challenge falls to chemists to develop greener alternatives or better recycling methods. In my own work, switching to less hazardous protecting groups, when possible, has cut down on post-reaction cleanup and made the lab safer. Waste minimization in this context isn’t just a box to tick—it streamlines workflows and improves morale.

Innovation Through Teamwork

Collaboration between industry and academic labs is pushing new methods every year. Research teams across the globe are retooling molecule-building strategies, chipping away at costs and risks. Upcoming trends lean on automation, predictive software, and high-throughput screening to speed up each synthetic step, making molecules like methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate more valuable as flexible intermediates. The ideas move fast, but it’s the carefully chosen starting materials that often tip projects from paper to reality.

What are the storage conditions for this compound?

Everyday Risks and What’s Really at Stake

People talk about proper storage of chemicals as if it’s just a detail for scientists behind thick lab doors. In truth, it matters for anyone who handles chemicals, even in places as familiar as a high school, a small business, a garage, or a doctor’s office. Storage missteps have consequences that spill beyond regulatory fines—fires, poisonings, business shutdowns, and enormous cleanup bills grow out of smaller mistakes. My own time working in manufacturing taught me to respect how fast situations can get out of hand if you forget the basics.

Practical Calls: Temperature and Humidity

The label on a container might recommend something like “store in a cool, dry place.” Sounds easy enough, though this kind of instruction gets skipped more than you’d think. For chemicals prone to breaking down or sparking reactions, this isn’t busywork. High temps speed up reactions inside a bottle, and moisture from the air sneaks into packaging, turning powdery solids into hard blocks or producing acids. More than once, I’ve watched colleagues struggle to get product out of a clumpy container, only to discover their expensive chemical spoiled for good.

Some compounds break down in the warmth of a regular storeroom. Others rust through their packaging if left in damp places—a single humid summer can ruin an entire inventory if the building lacks air conditioning or dehumidifiers. Flammable solvents stored above 25°C turn far more hazardous, building up pressure or leaking fumes. Common sense from years on the job says always check the recommended temperature—and if the data sheet calls for refrigeration or sub-zero storage, then ordinary shelving is out of the question.

Light and Air: Two Forgotten Enemies

Plenty of chemicals react to light long before you notice. Liquid peroxides, photographic reagents, and even some vitamins lose strength after sitting in daylight. One workplace incident I saw happened because a plain glass bottle sat on a sunny windowsill, only to burst a month later. This is why suppliers use brown or opaque bottles, but actual storage rooms need strongly limited light and sealed shelves. Oxygen in the air also causes invisible changes—metals grow unstable, powders discolor, or the label becomes unreadable from corrosion. The fix involves closing bottles tightly, and for some compounds, purging containers with nitrogen or another gas.

Separation: Keeping Danger at a Distance

Mixing things up in storage rarely ends well. Acids sitting next to bases, oxidizers near solvents—that setup reads like a recipe for disaster. I’ve seen firsthand how a broken acid bottle leaked fumes across a shelf, corroding nearby containers and launching an emergency evacuation. Splitting dangerous materials by type may sound tedious, but it’s key for safety. Color-coded bins, metal cabinets labeled “flammable,” or even caged-off spaces for poisons make a difference on the ground.

Training and Documentation: No Substitute

People tend to underestimate the value of written instructions and routine reminders. Unclear handwriting, missing labels, or tossed-out safety sheets spell trouble. Digital records and updated training keep everyone on the same page. If someone knows exactly what conditions protect a chemical, and they have the tools to pull it off, most problems never start. In factories and labs where I’ve worked, the best safety records go to crews that care about the details and check their storage daily.

Solutions That Stick

Smart storage comes from a blend of practical habits and respect for risk. Regular inspections, using temperature and humidity monitors, investing in real cabinets, and hiring experienced staff pay off over time. Regulatory compliance means more than just legal boxes ticked; it keeps people, profits, and the planet safer. Anything less, and everyone pays the price in the end.

How should I handle and dispose of this chemical safely?

The Real Risks Lurk in the Details

Most folks don't realize how easy it is to overlook chemical safety. I once found a forgotten container in my garage, the label nearly worn off. A little web research later, I learned even household products can cause big problems if tossed in the regular trash. Chemicals in cleaning agents, garden sprays, and automotive products sneak into soil or water if not handled with care.

Reading Labels Saves Trouble

Every chemical bottle has clues—sometimes warnings, symbols, or disposal rules. Those pictograms look small, but they spell out whether a substance burns, reacts, or causes harm on contact. Bleach may irritate skin, while old motor oil can carry heavy metals. Local authorities and the Environmental Protection Agency (EPA) offer plenty of information in plain language. Don’t be afraid to make a quick call to your city’s waste center, since they always know about options in your area and what products to keep separate.

No Pouring or Dumping

It’s tempting to dump leftover paint down the sink, but that often causes more harm than good. Many cities fine for chemicals in drains, and septic systems just aren’t built to filter toxins. I’ve noticed spills spread, soaking into the ground where pets and children play, and leaks can end up in streams. Pouring outside is no solution, either. Even small quantities build up in ecosystems.

Proper Storage Makes a Difference

Before deciding what to do with the stuff, put on gloves and find a box or tub that keeps the original container upright and away from anything flammable. Sometimes, it’s a matter of keeping the garage ventilated and away from direct sunlight. I keep all leftover substances on one shelf, out of reach from little ones. That way, accidents are less likely, and I can check expiration dates when tackling another clean-up project.

Community Drop-Offs and Take-Back Programs

Many towns run hazardous waste days, letting residents drive in and hand off stuff like solvents, pesticides, batteries, and even old propane tanks. Check your city or county website for schedules or recycling centers that handle special materials. Pharmacies and hardware stores sometimes accept specific chemicals, making disposal part of everyday errands.

Donating, Sharing, or Reusing

If you have unopened or still-useful products, see if a neighbor or local organization could use them up safely. Art studios, schools, or nonprofits sometimes look for supplies like paint and cleaning products. It’s better than letting good material go bad or sitting for years under the sink.

Trust Science, Not Guesswork

I was tempted once to mix leftover chemicals, hoping to reduce clutter fast. Mixing makes reactions much more likely, especially if containers lack labels or dates. Stories abound about burns, fumes, or worse from folks in a hurry. If instructions are faded or missing, online resources like the EPA’s guide for household hazardous waste make identifying and handling things straightforward.

Responsible Habits Protect Home and Community

Respecting chemical risks shows care for friends, family, and neighbors. Regularly checking storage areas, using leftovers thoughtfully, and contacting local experts protects air, water, and health. Little steps add up, and the extra effort pays off in peace of mind, knowing no one will stumble across a nasty surprise years down the line.

What is the purity of the product supplied?

Why Purity Shapes Quality

Purity isn’t just a line on a certificate—it's what separates reliable materials from the sort that cut corners. Whenever I hear companies tout numbers on purity, I remember a time I worked on a project that stalled because an ingredient arrived with lower purity than expected. Nobody checked. We lost two weeks and trust. A product’s quality hinges on what’s really inside—no filler or hidden contaminant allowed.

Hidden Costs of Overlooking Purity

Impurities don’t just water down a product. They cause reactions to go sideways, lead machines to clog, or set off safety alarms in a lab. One out-of-spec batch sparks recalls and angry phone calls. According to the U.S. Pharmacopeia, failing to meet published purity levels can lead businesses to regulatory fines and even bans on their goods. Before a shipment leaves the dock, verifying purity can save thousands and safeguard reputations.

Behind the Purity Label

Product labels often read “99.5% pure” or boast even higher figures. That percentage points to the fraction that matches what buyers ordered. The rest, even in tiny amounts, matters. Safety data sheets and certificates of analysis list impurities, but not everyone reads them. One time, a client ran a test only to find a persistent contaminant derailing results—fine print fooled them. The best practice is to request third-party testing or review data from multiple batches.

Why Verification Beats Assumptions

Every industry treats purity with different standards. For food, the FDA offers clear rules on ingredients and tolerable contaminants. Pharmaceutical companies adhere to strict limits, with the FDA requiring validated lab methods. In electronics, even a fraction of a percent impurity in a semiconductor throws off conductivity. Skipping validation steps runs the risk of delivering ineffective products or worse, putting users at risk.

Building Trust Through Transparency

Buyers deserve clear answers. A trusted supplier backs claims with documented data—batch numbers, lab reports, and even open communication about slight variations. I once worked with a supplier who gave clear, real-time updates on quality test results. The peace of mind knowing exactly what was arriving meant delays dropped off, so did hands-on troubleshooting. That level of honesty builds long-term trust.

Solutions That Prove Purity

Today, modern labs offer advanced testing—gas chromatography, spectroscopy, and mass spectrometry spot even traces of contaminants. These tests help keep impurity levels in check, and allow buyers to hold suppliers to their word. Investing in verification gives better results than relying on surface claims. Building strong supplier partnerships makes it easier to catch issues before they pose a threat, saving time, money, and reputation.

Purity shapes every outcome. From supply chains to science labs, the numbers behind every product matter far more than the boldface claim on a website. Putting in effort to check, question, and confirm where it counts stops problems before they start.

What solvents are recommended for dissolving this compound?

Everyday Impact of Solvent Choices

The question, “What solvents are recommended for dissolving this compound?” might sound like it only matters to chemists in white coats, but the answer matters far beyond the lab. The decision actually steers the safety of medicines, the effectiveness of cleaning supplies, the development of new materials, and even the way artists mix their paints. People buy products every day trusting that someone upstream thought through this choice. Poor solvent selection leads to health risks, wasted money, or products that just don’t work.

The Science Drives the Choice

Picking a solvent starts with understanding the structure of the compound. “Like dissolves like”—a phrase most college students remember—actually stands up in real-world use. For a greasy, oil-based molecule, something like hexane or toluene cuts through it. Water never stands a chance here, which anyone who’s tried to rinse an oily pan knows firsthand. On the flip side, water dissolves salty or sugary compounds without any fancy equipment.

Polarity isn’t the only piece of the puzzle. Boiling point and volatility matter, especially in large scale or home settings. Take acetone—used for everything from nail polish remover to cleaning lab glassware. It dries quickly, leaves almost nothing behind, and most folks tolerate the odor. Other solvents linger or create real safety problems: benzene carries serious cancer risks even at low exposures. That’s not something to shrug off at scale or in a home workshop.

Health, Environment, and Regulations

Solvent choices aren’t just about molecules. Regulations shape what ends up in industry, stores, and even schools. The FDA, EPA, and OSHA pay attention to solvents in drug manufacturing or cleaning products. Years ago, chloroform popped up in pharmaceuticals and cough syrups. Now, you won’t see it because of its toxic effects—and safer alternatives have taken its place. California’s tough air quality laws drove industry toward low-VOC paints and adhesives, even though companies complained at first. Regular people get cleaner air as a result.

Environmental stories drive change too. Look at the shift away from halogenated solvents, like trichloroethylene. These used to be industry favorites for degreasing metal parts, but contamination and health studies forced manufacturers to switch to aqueous-based cleaners and safer organics. A small change in the textbook can make a big difference on a county’s water quality.

Finding Fixes and Moving Forward

Scientists now balance solubility needs with greener chemistry goals. I’ve watched progress happen in real-time—green chem classes train students to weigh toxicity, persistence in the environment, and human exposure alongside price and performance. Tools like the Sigma-Aldrich Solvent Selection Guide or the CHEM21 selection table help researchers avoid the worst hazards before they even pour the first milliliter.

Consumer pressure matters. People ask about “clean beauty” or “eco-friendly cleaners.” Makers of those products rethink their solvents. Once, products boasting “ethanol from corn” would be laughed out of a lab—now those same renewable choices get marketing campaigns.

The search for the perfect solvent won’t end. Better education, tighter regulations, and honest labels push us forward. People want products that work, don’t pollute, and won’t make them sick. Everyone wins when companies and scientists keep working toward that target.

Methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate
Methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate
Methyl (3R)-3-[(tert-butyldimethylsilyl)oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate