Benzyl 3-deoxy-3-(3,4,5-trimethoxybenzylamino)-β-L-xylopyranoside

Reaction of 3,4,5-trimethoxybenzylamine and benzyl 2,3-anhydro-β-L-ribopyranoside in refluxing ethanol produced benzyl 3-deoxy-3-(3,4,5-trimethoxybenzylamino)-β-L-xylopyranoside in 72.5% yield. An attempt to synthesize the title compound by reacting neat 3,4,5-trimethoxybenzylamine with benzyl 2,3-anhydro-β-L-ribopyranoside without a solvent produced a dark brown mixture with several decomposition products. The structure of benzyl 3-deoxy-3-(3,4,5-trimethoxybenzylamino)-β-L-xylopyranoside was determined using elemental analysis, 1H-NMR and 13C-NMR and its conformation is 1 C 4 .