REVISION, BY PROTON, C-13, AND N-15 NMR-SPECTROSCOPY, OF THE STRUCTURE ASSIGNED A BIS(HEXOPYRANOSYL)-AMINE DERIVATIVE

Structural analysis of the acetylated, minor product of the reaction of methyl 2,3-anhydro-4,6-O-benzylidene-α-d-mannopyranoside with ammonia by high-field proton- and 13C-n.m.r. spectroscopy, and also 15N-n.m.r. spectroscopy, has shown that this acetyl derivative is bis(methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-yl)amine , and not the N-acetyl derivative reported previously. The configuration and conformation of the bis(altropyranosid-3-yl)amine derivative have been determined, and its unusually large 1J15NH coupling constant is discussed. © 1979.