Crystal structure of 3-C-(N-benzyloxycarbonyl)aminomethyl-3-deoxy-1,2:5,6-di-O-isopropylidene-α-d-allofuranose

Abstract

The title compound, C21H29NO7 (1) [systematic name: benzyl ({(3aR,5S,6R,6aR)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl)carbamate], consists of a substituted 2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxolane skeleton. The furanose ring adopts an envelope conformation close to C3-exo, where the C atom substituted by the benzyl carbamate group is the flap. The fused dioxolane ring also adopts an envelope conformation, as does the terminal dioxolane ring, with in each case an O atom as the flap. In the crystal, molecules are linked by N—H...O and C–H...O hydrogen bonds, forming chains propagating along the b-axis direction.

Keywords

• crystal structure
• 3-aminomethyl diacetone-D-allose
• imino sugar precursor
• sugar amino acid precursor
• hydrogen bonding.