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

J.M. Macdonald; Robert Stick

doi:10.1071/CH03228

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

J.M. Macdonald, Robert Stick

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6 Citations (Scopus)

Abstract

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 language	English
Pages (from-to)	449-453
Journal	Australian Journal of Chemistry
Volume	57
Issue number	5
DOIs	https://doi.org/10.1071/CH03228
Publication status	Published - 2004

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title = "The Synthesis of a D-Glucose-like Piperidin-2-one: Isofagomine Lactam",

abstract = "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.",

author = "J.M. Macdonald and Robert Stick",

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journal = "Australian Journal of Chemistry",

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T1 - The Synthesis of a D-Glucose-like Piperidin-2-one: Isofagomine Lactam

AU - Macdonald, J.M.

AU - Stick, Robert

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N2 - 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.

AB - 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.

U2 - 10.1071/CH03228

DO - 10.1071/CH03228

M3 - Article

SN - 0004-9425

VL - 57

SP - 449

EP - 453

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 5

ER -

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

Abstract

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