Studies of Antibiotics and Related Substances. XXXI. The Synthesis of Kanamycin-6′-phosphate

The introduction of a phosphate group into the 3-amino-3-deoxy-d-glucose moiety of kanamycin, a useful antibiotic, has been described. Tetra-N-anisylidene kanamycin was treated with diphenyl phosphorochloridate. Hydrolysis of the product followed by hydrogenolysis afforded kanamycin-6′-phosphate in a good yield. An alternative phosphorylation of kanamycin via tetra-N-carbobenzoxykanamycin to hexa-O-acetyl-tetra-N-carbobenzoxy-6′-diphenylphosphoro-kanamycin was described, however, the removal of the all protecting groups except the phosphate group encountered a difficulty.