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

Full Text: HTML

Citation Number: 102

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.

Related Articles:

All eight stereoisomeric d-glyconic-δ-lactams: synthesis, conformational analysis, and evaluation as glycosidase inhibitors

[Nishimura, Yoshio; Adachi, Hayamitsu; Satoh, Takahiko; Shitara, Eiki; Nakamura, Hikaru; Kojima, Fukiko; Takeuchi, Tomio Journal of Organic Chemistry, 2000 , vol. 65, # 16 p. 4871 - 4882]

A facile transformation of sugar lactones to azasugars

[Overkleeft, Herman S.; Wiltenburg, Jim van; Pandit, Upendra K. Tetrahedron, 1994 , vol. 50, # 14 p. 4215 - 4224]

Total synthesis of deoxymannojirimycin and D-mannolactam via carbonylation of 5-vinyloxazolidin-2-ones

[Knight, Julian G.; Tchabanenko, Kirill Tetrahedron, 2003 , vol. 59, # 3 p. 281 - 286]

All eight stereoisomeric d-glyconic-δ-lactams: synthesis, conformational analysis, and evaluation as glycosidase inhibitors

[Journal of Organic Chemistry, , vol. 65, # 16 p. 4871 - 4882]

Enantiospecific synthesis of D-mannono-δ-lactam from vitamin C

[Shing, Tony K. M. Journal of the Chemical Society, Chemical Communications, 1988 , # 18 p. 1221]

More Articles...