Trimethylsilyl trifluoromethanesulfonate

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Trimethylsilyl trifluoromethanesulfonate
IUPAC name

trimethylsilyl trifluoromethanesulfonate

Other names

TMSOTf
Trimethylsilyl triflate
TMS triflate
Trifluoromethanesulfonic acid trimethylsilyl ester

Identifiers
CAS number 27607-77-8
PubChem 65367
Jmol-3D images {{#if:C[Si](C)(C)OS(=O)(=O)C(F)(F)F|Image 1
Properties
Molecular formula C4H9F3O3SSi
Molar mass 222.25 g/mol
Except where noted otherwise, 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

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

References

  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
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