Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

Abhijit S. Bhat, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

Reported herein is a general method for the efficient syntheses of a variety of β-cyano glycosides through the activation of per-O-trimethylsilyl glycosides with TMSI to form α-glycosyl iodides, which undergo SN2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)6 in THF/H2O to give the corresponding aminomethyl glycosides.

Original languageEnglish (US)
Pages (from-to)2081-2084
Number of pages4
JournalOrganic Letters
Volume3
Issue number13
DOIs
StatePublished - Jun 28 2001
Externally publishedYes

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monosaccharides
glucosides
Monosaccharides
Disaccharides
Iodides
Glycosides
iodides
synthesis
cyanides
Chemical activation
activation

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides. / Bhat, Abhijit S.; Gervay-Hague, Jacquelyn.

In: Organic Letters, Vol. 3, No. 13, 28.06.2001, p. 2081-2084.

Research output: Contribution to journalArticle

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