Bromide ion → HCID 13871700, compound

Participants

Reaction Steps

Briefly, Jespersen first described synthesis of IFG in a six step synthesis starting from 1,6:2,3-dianhydro-4-O-benzyl-β-D-mannopyranose. This method employed introducing a hydroxymethyl group at C-7 by epoxide opening with vinylmagensium bromide, followed by ozonolysis in ethanol to give 1,6-anhydro-4-O-benzyl-β-D-glucopyranose. Hydrolysis of the anhydro bond with sulfuric acid and oxidative carbon chain cleavage provided a pentodialdose, which was cyclized by reductive amination with ammonia to produce the 4-O-benzyl derivative of IFG. The protecting group was removed by hydrogenation under acid conditions (hydrogen and palladium-on-carbon) to produce the HCl salt of IFG.

Provenance & Evidence