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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Synthesis of a D-Glucose-like Piperidin-2-one: Isofagomine Lactam

James M. Macdonald and Robert V. Stick

Australian Journal of Chemistry 57(5) 449 - 453
Published: 07 May 2004

Abstract

Benzyl 4-cyano-4-deoxy-α-D-arabinoside was converted into both its2,3-di-O-acetyl and 2,3-di-O-(tert-butyldimethylsilyl)derivatives. The latter, by a process of hydrogenolysis, oxidation, and methanolysis, gave methyl2,3-di-O-(tert-butyldimethylsilyl)-4-cyano-4-deoxy-D-arabinonate. Reductionof this methyl ester with borane dimethyl sulfide gave, after deprotection, isofagomine lactam.

https://doi.org/10.1071/CH03228

© CSIRO 2004

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