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

TKM Shing

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

Full Text: HTML

Citation Number: 6

Abstract

An eight-step synthesis of the glycosidase inhibitor D-mannono-6-lactam from vitamin C is described. ... Very recently, the potential of polyhydroxylated 6-lactams as a new class of glycosidase inhibitors has been indicated.1 D-Mannono-6-lactam (1) , previously formed by microbial ... H o ~ - NH Ho--Po 0 "'I ... Scheme 1. Reagents: i, Pd, Ht, H20 (100%); ii, Me,CO/HCl then aq. AcOH (68%); iii, ButPh2SiC1, pyridine (95%); iv, (CF3S02),0, CH2C12, pyridine (92%); v, ...

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]

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

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

More Articles...