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General syntheses of ethyl 2-ulosonates and 3-deoxy-D-manno-oct-2-ulosonic acid from carbohydrate lactones with 1-ethoxyvinyllithium

✍ Scribed by Shende Jiang; Anthony D. Rycroft; Gurdial Singh; Xiang-Zhu Wang; Yu-Lin Wu

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 238 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00590-5

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✦ Synopsis

Reactions of l-ethoxyvinyllithium with isopropylidene or benzyl protected sugar lactones afforded the corresponding hemiacetals which, on ozonolysis, gave the ethyl 2-ulosonates. This allowed a rapid and efficient synthesis of 3-deoxy-D-manno-oct-2-ulosonic acid (KDO).

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