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Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO)

✍ Scribed by Frick, Wendelin ;Krülle, Thomas ;Schmidt, Richard R.

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
423 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

[(Benzyloxy)(benzyloxycarbonyl)methyl]triphenylphosphonium bromide (8), obtained from glyoxylic acid via a convenient one‐pot procedure, reacted in a Wittig reaction with 4‐O‐benzyl‐2,3:5,6‐di‐O‐isopropylidene‐D‐mannose (7), readily synthesized on a large scale from D‐mannose, to provide the KDO derivative 9. Hydrogenolytic removal of the benzyl groups furnished directly the 4,5:7,8‐di‐O‐isopropylidene protected KDO 11. Its treatment with diazomethane led to the known ester derivative 12α,ß (2:1 anomeric mixture) which could be also obtained by transesterification of 9 and subsequent hydrogenolytic debenzylation.

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