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Asymmetric Induction in the Epoxidation of Alkenyl Glycosides of Tri-O-acetyl-N-acetyl-β-D-glucosamine

✍ Scribed by Peter, Martin G. ;Boldt, Peter-c. ;Petersen, Stefan

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
583 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The reaction of alkenyl glycosides 2a–2c with MCPBA gives diasteroisomeric mixtures of epoxides 3 and 4. The asymmetric induction decreases in the order 2a ≫ 2b > 2c. The absolute configuration of epoxyalkyl glycosides is determined by correlation with (R)‐glycerinaldehyde in an independent synthesis of 3a and 3c.

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