A formal total synthesis of deoxynojirimycin from D-glucitol

Journal of the Brazilian Chemical Society

Universidade Estadual de Campinas, Campinas, Brazil¹  Kato, Lucilia¹  Braga, Raquel M.¹ 

关键词: D-glucitol;    glycosidase inhibitors;    isopropylidene derivatives;    deoxynojirimycin;   

DOI  :  10.1590/S0103-50532003000500019

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

This report deals with the formal synthesis of deoxynojirimycin using D-glucitol as an inexpensive starting material. Through a sequence of several selective protection/deprotection and nucleophilic substitution reactions, many isopropylidene derivatives were obtained. Formation of an epoxide intermediate and its subsequent ring opening, via intramolecular nucleophilic substitution, leads to the synthesis of heterocyclic 1,5-dideoxy-1,5-diamine-2,3-O-isopropylidene-6-silyl-D-glucitol, which is a precursor of deoxynojirimycin (DNJ).

【 授权许可】

Unknown