Studies of the synthesis of 1,2-cis-(cyclic carbamates) of α-D-aldopyranosylamines

Article abstract of DOI:10.1016/0008-6215(93)84206-L

Reaction of α-D-glucopyranosyl azide with triphenylphosphine and carbon dioxide gave 1-N,2-O-carbonyl-α-D-glucopyranosylamine (7) and its α-D-furanose analogue (1), and 1-N,3-O-carbonyl-α-D-allofuranosylamine (15) and its α-D-pyranose analogue (17).Similarly, α-D-xylopyranosyl azide gave 1-N,2-O-carbonyl-α-D-xylopyranosylamine (9) and its α-D-furanose analogue (3), and 1-N,3-O-carbonyl-α-D-ribopyranosylamine (19) and its β-D-xylopyranose analogue (21).The structures of the products and their acetylated derivatives were established by 1H and 13C NMR spectroscopy. 1-N,3-O-Carbonyl-β-D-xylopyranosylamine (21) was obtained from β-D-xylopyranosyl azide when spontaneous rearrangement of the 1,2-(cyclic carbamate) 5 into 21 occurred in water.