Deoxy‐nitrosugars. 4th communication. Convenient synthesis of 1‐deoxy‐1‐nitroaldoses
- 5 May 1983
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 66 (3) , 789-794
- https://doi.org/10.1002/hlca.19830660310
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.Keywords
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