Tetrahedron

Practical synthesis of deoxymannojirimycin and mannonolactam from L-gulonolactone.: Synthesis of L-deoxymannojirimycin and L-mannonolactam from D- …

GWJ Fleet, NG Ramsden, DR Witty

Index: Fleet, George W. J.; Ramsden, Nigel G.; Witty, David R. Tetrahedron, 1989 ,  vol. 45,  # 1  p. 319 - 326

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Citation Number: 101

Abstract

An eight step synthesis of deoxymannojirimycin from L-gulonolactone in 25% overall yield is reported the key step is the formation of a δ-lactam by the reduction of a 5-azidolactone. The preparations of mannonolactam front L-gulonolactone and of L-deoxymannojirimycin and L- mannonolactam from D-gulonolactone are described.