TY - JOUR
T1 - The Synthesis of a D-Glucose-like Piperidin-2-one: Isofagomine Lactam
AU - Macdonald, J.M.
AU - Stick, Robert
PY - 2004
Y1 - 2004
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
VL - 57
SP - 449
EP - 453
JO - Australian Journal of Chemistry:an international journal for chemical science
JF - Australian Journal of Chemistry:an international journal for chemical science
SN - 0004-9425
IS - 5
ER -