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Deoxy-nitrosugars. 4th communication. Convenient synthesis of 1-deoxy-1-nitroaldoses

✍ Scribed by Bernard Aebischer; Andrea Vasella

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
359 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A new synthesis of 1‐deoxy‐1‐nitroaldoses by ozonolysis of N‐glycosylnitrones according to the procedure of Bailey et al. is described. Based on the oxime 1, the mannofuranosylnitrones 3–5 were obtained in yields of 86–88% and the 1‐deoxy‐1‐nitromannose 6 in yields of 70–76%. In the same manner the 1‐deoxy‐1‐nitroaldoses 9, 12, 18, and 19 were prepared in yields of 61–90% from the oximes 7, 10, 14 and 15, the procedure being compatible with the presence of free hydroxy groups.

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