85272-31-7 Usage
Description
DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE) is a reagent used for the selective protection of polyhydroxy compounds, particularly 1,2-, 1,3-, and 1,4-diols. It allows for the formation of dialkylsilylene derivatives under mild conditions with high yields and can be easily deprotected using aqueous hydrofluoric acid in acetonitrile.
Uses
Used in Organic Synthesis:
DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE) is used as a protecting group reagent for 1,3-diols, enabling selective protection and deprotection under mild conditions. This selective protection is crucial for the synthesis of complex organic molecules, such as N-homoceramides.
Used in Carbohydrate Chemistry:
In the synthesis of α-galactosyl ceramides, DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE) is used as a selective α-galactosylation reagent, facilitating the formation of the desired glycosidic linkages.
Used in Nucleoside Protection:
DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE) is used as a protecting group for nucleosides during their synthesis. The procedure involves the sequential addition of the ditriflate and triethylamine to the nucleoside in DMF, with the choice of solvent being critical for the success of the reaction.
Overall, DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE) is a versatile reagent in the fields of organic synthesis, carbohydrate chemistry, and nucleoside protection, providing selective protection and deprotection of polyhydroxy compounds.
Preparation
by the treatment of di-t-butylchlorosilane
with trifluoromethanesulfonic acid, followed by distillation
(71% yield).
Check Digit Verification of cas no
The CAS Registry Mumber 85272-31-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,5,2,7 and 2 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 85272-31:
(7*8)+(6*5)+(5*2)+(4*7)+(3*2)+(2*3)+(1*1)=137
137 % 10 = 7
So 85272-31-7 is a valid CAS Registry Number.
85272-31-7Relevant articles and documents
Synthesis and Restricted Conformation of 3',5'-O-(Di-t-butylsilanediyl)ribonucleosides
Furusawa, Kiyotaka,Ueno, Katsuhiko,Katsura, Tatsuo
, p. 97 - 100 (2007/10/02)
The reaction of ribonucleosides with di-t-butylsilyl diester such as dinitrate, diperchlorate and ditriflate in DMF gave selectively 3',5'-O-(di-t-butylsilanediyl)ribonucleosides in high yield.The conformation analysis by 1H NMR spectroscopy and X-ray crystallography showed that the product has a restricted conformation analogous to that observable in 3',5'-cyclic nucleotides.
