Acetic Acid → N-Benzhydryl-1-deoxynojirimycin

Participants

Reaction Conditions

Reaction Steps

To a -78° C. solution of 5-keto-D-glucose (Formula V, 4.00 g, 0.0225 mol) in 100 mL of methanol was added a cooled solution (-78° C.) of benzhydrylamine (3.29 g, 0.018 mol) and acetic acid (1.08 g, 0.018 mol) in 100 mL of methanol. Sodium cyanoborohydride (2.82 g, 0.0449 mole) was added, and the mixture was stirred at -78° C. for 2 h and then slowly warmed to ambient temperature. After 18 h, the solution was concentrated, saturated aqueous sodium carbonate was added, and the product was extracted into chloroform. The chloroform extracts were combined, dried (sodium sulfate), and concentrated to afford a yellow foam. Chromatographic purification on flash silica gel (5-10% gradient of methanol in chloroform) afforded 4.06 g (69%) of the title compound as a very pale yellow foam. 1H NMR and reversed-phase analytical HPLC showed that this substance was >95% stereochemically pure (ca. 4.5% of the iditol isomer). Recrystallization from MEOH afforded white needles, mp 101°-104° C. (corrected). Both 1H and 13C NMR in CDCl3 and D3CC(O)CD3 confirmed the structure.

Provenance & Evidence