Trimethylsilyl trifluoromethanesulfonate

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Trimethylsilyl trifluoromethanesulfonate
Trimethylsilyl trifluoromethanesulfonate2.svg
IUPAC name
trimethylsilyl trifluoromethanesulfonate
Other names
Trimethylsilyl triflate
TMS triflate
Trifluoromethanesulfonic acid trimethylsilyl ester
3D model (JSmol)
ECHA InfoCard 100.044.136
Molar mass 222.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethylsilyl trifluoromethanesulfonate is a trifluoromethanesulfonate derivate with a trimethylsilyl R-group. It has similar reactivity to trimethylsilyl chloride, and is also used often in organic synthesis.

Examples of use[edit]

The stereoselective synthesis of seven benzylated proanthocyanidin trimers (epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (procyanidin C1), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (procyanidin C2), 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.[1]

It has been used in Takahashi Taxol total synthesis or for chemical glycosylation reactions.

See also[edit]


  1. ^ Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. Akiko Saito, Akira Tanaka, Makoto Ubukata and Noriyuki Nakajima, Synlett, 2004, volume 6, pages 1069-1073, doi:10.1055/s-2004-822905