Trimethylsilyl trifluoromethanesulfonate is a
trifluoromethanesulfonate
In organic chemistry, triflate (Preferred IUPAC name, systematic name: trifluoromethanesulfonate), is a functional group with the Chemical formula, formula and Chemical structure, structure . The triflate group is often represented by , as oppo ...
derivate with a
trimethylsilyl
A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom minus;Si(CH3)3 which is in turn bonded to the rest of a molecule. This structural group is ch ...
R-group. It has similar reactivity to
trimethylsilyl chloride
Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound ( silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. ...
, and is also used often in organic synthesis.
Illustrative reactions
A common application is the conversion of ketones and aldehydes to silyl enol ethers.
The stereoselective synthesis of seven benzylated proanthocyanidin trimers (epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (
procyanidin C1
Procyanidin C1 (PCC1) is a B type proanthocyanidin. It is an epicatechin trimer found in grape (''Vitis vinifera''), unripe apples, and cinnamon.
Natural occurrence and function
Procyanidin C1 can be isolated from grape seed extract.
Chemical ...
), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (
procyanidin C2
Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin.
Natural occurrences
Procyanidin C2 is found in grape seeds (''Vitis vinifera'') and wine, in barley (''Hordeum vulgare''), malt and beer, in ''Betula spp.'', in ''P ...
), epicatechin-(4β-8)-epicatechin-(4β-8)-catechin trimer and epicatechin-(4β-8)-catechin-(4α-8)-epicatechin trimer derivatives) can be achieved with TMSOTf-catalyzed condensation reaction, in excellent yields. Deprotection of (+)-catechin and (−)-epicatechin trimers derivatives gives four natural procyanidin trimers in good yields.
It has been used in
Takahashi Taxol total synthesis
The Takahashi Taxol total synthesis published by Takashi Takahashi in 2006 is one of several methods in taxol total synthesis.''A Formal Total Synthesis of Taxol Aided by an Automated Synthesizer'' Takayuki Doi, Shinichiro Fuse, Shigeru Miyamoto, ...
or for
chemical glycosylation
A chemical glycosylation reaction involves the coupling of a glycosyl donor, to a glycosyl acceptor forming a glycoside. If both the donor and acceptor are sugars, then the product is an oligosaccharide. The reaction requires activation with a s ...
reactions.
Trimethylsilyl trifluoromethanesulfonate is used to install tert-alkyl groups on phosphine (R = alkyl):
:PH
3 + R
3C–OAc + Me
3SiOTf →
R3C)2PH2Tf
Related reagents
Trimethylsilyl trifluoromethanesulfonate is a source of trimethylsilyl cation. Other more potent sources silylium cations are known.
See also
*
Silyl enol ether
Silyl enol ethers in organic chemistry are a class of organic compounds that share a common functional group composed of an enolate bonded through its oxygen end to an organosilicon group. They are important intermediates in organic synthesis.
Syn ...
References
Trimethylsilyl compounds
Triflate esters
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