Syntheses of Neamine and Its Diastereomer; the Condensation of Protected 2, 6-Diamino-2, 6-dideoxy-α-D-glucopyranosyl Bromide with a 2-Deoxystreptamine Derivative

抄録

3, 4-Di-O-acetyl-2, 6-dideoxy-2-(2', 4'-dinitroanilino)-6-phthalimido-α-D-glucopyranosyl bromide (I) was prepared in a good yield from glucosamine hydrochloride. A modified Königs-Knorr condensation of this bromide with a 2-deoxysteptamine derivative afforded a neamine derivative (IX) and its diastereomer (X). These compounds, (IX) and (X), were identified by PMR spectroscopy after conversion into the corresponding N-acetyl derivatives, (XI) and (XII).