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

J.M. Macdonald, Robert Stick

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


Benzyl 4-cyano-4-deoxy-alpha-D-arabinoside was converted into both its 2,3-di-O-acetyl and 2,3-di-O-(tertbutyldimethylsilyl) derivatives. The latter, by a process of hydrogenolysis, oxidation, and methanolysis, gave methyl 2,3-di-O-(tert-butyldimethylsilyl)-4-cyano-4-deoxy-D-arabinonate. Reduction of this methyl ester with borane dimethyl sulfide gave, after deprotection, isofagomine lactam.
Original languageEnglish
Pages (from-to)449-453
JournalAustralian Journal of Chemistry
Issue number5
Publication statusPublished - 2004


Dive into the research topics of 'The Synthesis of a D-Glucose-like Piperidin-2-one: Isofagomine Lactam'. Together they form a unique fingerprint.

Cite this