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

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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, ...