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Stereoselective Synthesis of C- and N-Ketosides by Lewis Acid-Catalyzed C- and N-Glycosidation of Alkynyl, Phenyl, and Methyl Ketoses

✍ Scribed by Ana M. Gómez; Clara Uriel; Slawomir Jarosz; Serafín Valverde; J. Cristóbal López

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 196 KB
Volume: 2003
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200300465

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✦ Synopsis

Abstract

C‐Ketosides can be prepared conveniently, in a stereoselective manner, from alkynyl, phenyl and methyl glucopyranose hemiketals by reaction with carbon nucleophiles in the presence of Lewis acids. The reaction of the hemiketals with trimethylsilyl azide provides an efficient route to the corresponding N‐ketopyranosides. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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