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262021

Di-tert-butylsilyl bis(trifluoromethanesulfonate)

Name: Di-<I>tert</I>-butylsilyl bis(trifluoromethanesulfonate)
Brand: ALDRICH

97%

Synonym(s):

DTBS ditriflate, Di-tert-butylsilyl ditriflate, Trifluoromethanesulfonic acid di-tert-butylsilylene ester

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About This Item

Linear Formula:

(CF₃SO₃)₂Si[C(CH₃)₃]₂

CAS Number:

85272-31-7

Molecular Weight:

440.45

UNSPSC Code:

12352302

NACRES:

NA.22

PubChem Substance ID:

24855853

MDL number:

MFCD00010581

Beilstein/REAXYS Number:

3569211

Assay:

97%

Form:

liquid

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Properties

Quality Level

200

assay

97%

form

liquid

refractive index

n20/D 1.398 (lit.)

bp

73-75 °C/0.35 mmHg (lit.)

density

1.352 g/mL at 25 °C (lit.)

functional group

fluoro, triflate

SMILES string

CC(C)(C)[Si](OS(=O)(=O)C(F)(F)F)(OS(=O)(=O)C(F)(F)F)C(C)(C)C

InChI

1S/C10H18F6O6S2Si/c1-7(2,3)25(8(4,5)6,21-23(17,18)9(11,12)13)22-24(19,20)10(14,15)16/h1-6H3

InChI key

HUHKPYLEVGCJTG-UHFFFAOYSA-N

Description

General description

Di-tert-butylsilyl bis(trifluoromethanesulfonate), also known as di-tert-butylsilyl ditriflate, that easily reacts with hydroxylic solvents. It is commonly used as a protecting group for diols in oligonucleotide synthesis.

Application

Di-tert-butylsilyl bis(trifluoromethanesulfonate) is used:

As a Boekelheide promoter to synthesize pyrrolidines and piperidines via intramolecular cyclization.
As a protecting group reagent for 1,3-diols used recently in a synthesis of N-homoceramides.
For selective α-galactosylation in the synthesis of α-galactosyl ceramides.