
%0 Journal Article
%A Macdonald, James M. 
%A Stick, Robert V. 
%T The Synthesis of a <emph type="6">D</emph>-Glucose-like Piperidin-2-one: Isofagomine Lactam
%J Australian Journal of Chemistry
%D 2004/05/06
%V 57
%N 5
%P 449-453
%K 
%R https://doi.org/10.1071/CH03228
%U https://www.publish.csiro.au/paper/CH03228 
%X Benzyl 4-cyano-4-deoxy-&#945;-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. 
