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Synthesis of Methyl 2-O-Benzyl-6-deoxy-3-c-methyl-α-D-mannopyranoside and Methyl α-D-Evalopyranoside

✍ Scribed by Žagar, Cyrill ;Scharf, Hans-Dieter

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

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✦ Synopsis

Abstract

Methyl 2‐O‐benzyl‐6‐deoxy‐3‐C‐methyl‐α‐D‐mannopyranoside (2) was synthesized in ten steps by starting from the readily available methyl 2,3‐anhydro‐4,6‐O‐benzylidene‐α‐D‐allo‐pyranoside (3). The key step was the stereoselective cis‐hydroxylation (cat. osmium(VIII) oxide) of methyl 2‐O‐benzyl‐4,6‐O‐benzylidene‐3‐deoxy‐3‐C‐methylene‐α‐D‐arabino‐hexo‐pyranoside (9), producing methyl 2‐O‐benzyl‐4,6‐O‐benzylidene‐3‐C‐hydroxymethyl‐α‐D‐mannopyranoside (11) and its C‐3 epimer in a ratio of 20: 1. Catalytic hydrogenation of 2 gave methyl 6‐deoxy‐3‐C‐methyl‐α‐D‐mannopyranoside (methyl‐α‐D‐evalopyranoside, 1).

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