A formal total synthesis of deoxynojirimycin from D-glucitol

Journal of the Brazilian Chemical Society

Raquel M. Braga¹  Lucilia Kato¹ 

[1] ,Universidade Estadual de Campinas Instituto de Química Campinas SP ,Brazil

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

DOI  :  10.1590/S0103-50532003000500019

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】

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