A formal total synthesis of deoxynojirimycin from D-glucitol

Abstract

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).

Keywords

• D-glucitol
• glycosidase inhibitors
• isopropylidene derivatives
• deoxynojirimycin