Preparation of 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-gluconic acid and its derivatives

Abstract

6-Amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-gluconic acid (I) was prepared by catalytic reduction of 6-azido-6-deoxy-2,3,4,5-tetra -O-methyl-D-gluconic acid (XVI) obtained by alkaline hydrolysis of the corresponding dimethylamine VIII or a mixture of dimethylamide VIII, amide XIV and methylamide XV. Amides VIII, XIV and XV are the products of alkylation of 6-azido-6-deoxy-D-gluconamide (VII) or 6-azido-6-deoxy-3,5-di-O-methyl-D-gluconamide (XIII), carried out with methyl iodide and silver oxide in N,N-dimethylformamide. Amides VII and XIII were prepared by amonolysis of 6-azido-6-deoxy-D-glucono-1,5-lactone (III) or 6-azido-6-deoxy-3,5-di-O-methyl-D-glucono-1,4-lactone (XII). Methylation of 6-amino-6-deoxy-D-gluconolactam (II) with methyl iodide and silver oxide in N,N-dimethylformamide afforded 6-deoxy-2,3,4,5-tetra-O-methyl-6-methylamino-D-gluconolactam (V) from which 6-deoxy-2,3,4,5-tetra-O-methyl-6-methylamino-D-gluconic acid (VI) was prepared.