Abstract
The preparation of the title compounds from the respective methyl 3-acetamido-3-deoxy-α-D-hexopyranosides was described. Introduction of an amino group at C6 was confirmed by nuclear magnetic resonance spectroscopy and dissociation constants. De-N-acetylation of methyl 3-acetamido-6-azido-3, 6-dideoxy-α-D-glucopyranoside by hydrazine was accompanied with reduction of the azido group to give directly methyl 3, 6-diamino-3, 6-dideoxy-α-D-glucopyranoside. Treatment of methyl 3-acetamido-3-deoxy-2, 6-di-O-p-tolylsulfonfl-α-D-glucopyranoside with sodium azide afforded, via an 2, 3-oxazolinium intermediate, methyl 3-acetamido-6-azido-3, 6-dideoxy-α-D-mannopyranoside. The isolation of a new compound, methyl 3-amino-3-deoxy-β-L-glucopyranoside from nitromethane condensation products was added.
