Synthetic Studies on Carbohydrate Antibiotics

Part VII Conversion of Methyl 3-Amino-3-deoxy-α-D-mannopyranoside to Methyl 3-Amino-3-deoxy-α-D-glucopyranoside

抄録

As an approach to the synthesis of α-D-glucopyranosides, the conversion of α-D-man-nopyranosides to α-D-glucopyranoside was studied. Methyl 3-benzamido-4, 6-O-benzylidene-3-deoxy-α-D-mannopyranoside (II) was oxidized to methyl 3-benzamido-4, 6-O-benzylidene-3-deoxy-α-D-arabino-hexosid-2-ulose (III). Reduction of III gave methyl 3-benzamido-4, 6-O-benzylidene-3-deoxy-α-D-glucopyranoside (IVa).