Trimethylsilyl trifluoromethanesulfonate

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Trimethylsilyl trifluoromethanesulfonate
Trimethylsilyl trifluoromethanesulfonate2.svg
Names
IUPAC name
trimethylsilyl trifluoromethanesulfonate
Other names
TMSOTf
Trimethylsilyl triflate
TMS triflate
Trifluoromethanesulfonic acid trimethylsilyl ester
Identifiers
3D model (JSmol)
ECHA InfoCard 100.044.136
Properties
C4H9F3O3SSi
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]

References[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