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Silyl ether information


General structure of a silyl ether

Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. The general structure is R1R2R3Si−O−R4 where R4 is an alkyl group or an aryl group. Silyl ethers are usually used as protecting groups for alcohols in organic synthesis. Since R1R2R3 can be combinations of differing groups which can be varied in order to provide a number of silyl ethers, this group of chemical compounds provides a wide spectrum of selectivity for protecting group chemistry. Common silyl ethers are: trimethylsilyl (TMS), tert-butyldiphenylsilyl (TBDPS), tert-butyldimethylsilyl (TBS/TBDMS) and triisopropylsilyl (TIPS). They are particularly useful because they can be installed and removed very selectively under mild conditions.

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Silyl ether

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Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. The general structure is R1R2R3Si−O−R4...

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Silyl enol ether

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In organosilicon chemistry, silyl enol ethers are a class of organic compounds that share the common functional group R3Si−O−CR=CR2, composed of an enolate...

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Organosilicon chemistry

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extremely unstable. Silyl ethers have the connectivity Si-O-C. They are typically prepared by the reaction of alcohols with silyl chlorides: (CH 3) 3SiCl...

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Tips

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Science, a journal in the Trends series Triisopropylsilyl, a type of silyl ether Triisopropylsilane, a hydrosilane Turkish Institute for Police Studies...

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Negative hyperconjugation in silicon

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the most industrially-important silicon α‑effect instead occurs with silyl ethers. Under hydrolysis condition, certain α-silane-terminated prepolymers...

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Silylation

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silylation is employed to protect OH and NH groups. The derivatives, silyl ethers and silyl amides, are resilient toward many reagents that would attack their...

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Brook rearrangement

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direction, these silyl migrations produce silyl ethers as products which is driven by the stability of the oxygen-silicon bond. The silyl substituents can...

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Ether

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Ge, Sn, Pb). Such compounds are considered ethers as well. Examples of such ethers are silyl enol ethers R3Si−O−CR=CR2 (containing the Si−O−C linkage)...

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Lovastatin

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to give a separable mixture of the starting lactone and the silyl ether. The silyl ether on hydrogenolysis followed by Collins oxidation gave the aldehyde...

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Silanol

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alkali. The alkoxysilanes (silyl ethers) of the type R3Si(OR') are slow to hydrolyze. Compared to the silyl ethers, silyl acetates are faster to hydrolyze...

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Polyester

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ketene dimers.⁠ Silyl method In this variant of the HCl method, the carboxylic acid chloride is converted with the trimethyl silyl ether of the alcohol...

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Silyl modified polymers

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gel state to a solid. Curing entails crosslinking by the hydrolysis of silyl ethers: 2 RSi(OCH3)2R' + H2O → [RSi(OCH3)R']2O + 2 CH3OH In a hydrolysis reaction...

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Rubottom oxidation

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Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxyacids to give the corresponding α-hydroxy carbonyl product...

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TASF reagent

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It is an anhydrous source of fluoride and is used to cleave silyl ether protective groups. Many other fluoride reagents are known, but few are...

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Nanomaterials

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size of the particle can be controlled by varying the concentration of silyl ether and alcohol or the micro emulsion method. Mesoporous silica nanoparticles...

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Functional group

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-magnesium halide methylmagnesium chloride Alkylaluminium Al2R6 -aluminium trimethylaluminium Silyl ether R3SiOR -silyl ether trimethylsilyl triflate...

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Vinyltriethoxysilane

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Vinyltriethoxysilane is an organosilicon compound with the formula (C2H5O)3SiCH=CH2. It is a colorless liquid. The compound is bifunctional, featuring...

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Mukaiyama aldol addition

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addition is an organic reaction and a type of aldol reaction between a silyl enol ether (R2C=CR−O−Si(CH3)3) and an aldehyde (R−CH=O) or formate (R−O−CH=O)...

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Reductions with hydrosilanes

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hydrosilylation in the presence of hydrosilanes and fluoride. The resulting silyl ethers can be hydrolyzed with 1 M hydrochloric acid. Optimal yields of the hydrosilylation...

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Trimethylsilyl group

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materials are acetaldehyde and benzophenone which are both converted to silyl enol ether by reaction with tris(trimethylsilyl)silane and triflic acid with evolution...

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Trimethylsilyl iodide

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preferred due to its lower cost. TMSI reacts with alkyl ethers (ROR′), forming silyl ethers (ROSiMe3) and iodoalkanes (RI) that can be hydrolyzed to...

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Hexamethyldisiloxane

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acid catalyst, it converts alcohols and carboxylic acids into the silyl ethers and silyl esters, respectively. It reacts with rhenium(VII) oxide to give...

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Hydrosilylation

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and alkynes give alkyl and vinyl silanes; aldehydes and ketones give silyl ethers. Hydrosilylation has been called the "most important application of platinum...

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