A Facile, Practical Synthesis of 2,6-Dideoxy-2,6-imino-7-O-β-D-glucopyranosyl-D-glycero-L-gulo-heptitol (MDL 25,637)

Article abstract of DOI:10.1021/jo00272a015

A facile synthetic route useful for large-scale preparation of the α-glucosidase inhibitor, 2,6-dideoxy-2,6-imino-7-O-β-D-glucopyranosyl-D-glycero-L-gulo-heptitol (1), is described.The protected heptononitrile 5, prepared in three steps from the readily available bisulfite adduct of nojirimycin (2), was stereospecifically converted to carboxylic acid 6 by acid hydrolysis (90percent TFA/Hg(TFA)2) and oxidation (N2O4).After reduction, the resultant amino alcohol 7 was N-protected and condensed with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate to provide glucoside 9.Stepwise deprotection of 9 with transfer hydrogenation and base-catalyzed hydrolysis gave compound 1 in 26percent overall yield from 2.