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Synthesis of Thromboxane A2 Models from Glucose. II. Epoxidation Studies of Hex-2-enopyranosides

✍ Scribed by Cirelli, Alicia Fernández ;Moradei, Oscar ;Thiem, Joachim

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 458 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970926

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✦ Synopsis

Abstract

The synthesis of halohydrin 7, a potential precursor of the heterocyclic moiety of thromboxane A~2~ (TXA~2~) is described. Claisen‐Meerwein‐Eschenmoser rearrangement of hex‐3‐enopyranosides 4 and 8 yields the branched olefin sugars 5 and 9. Epoxidation studies with perbenzimidic acid (Payne's method) and m‐chloroperbenzoic acid (Anderson's method) were performed. Under treatment of the 2,3‐anhydrosugar 6 with LiBr, the epimeric halohydrins 7 and 10 were obtained in a ratio of 3:2.

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