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262021

Sigma-Aldrich

Di-tert-butylsilyl bis(trifluoromethanesulfonate)

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:
Molecular Weight:
440.45
Beilstein:
3569211
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

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

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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.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Zeitschrift fur Anorganische und Allgemeine Chemie, 618, 144-144 (1992)
Tetrahedron Letters, 23, 4871-4871 (1982)
Chemische Berichte, 125, 47-47 (1992)
Synlett, 2379-2379 (2006)
A new sequential intramolecular cyclization based on the boekelheide rearrangement
Assunta M,et al.
European Journal of Organic Chemistry (2011)

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