Studies of Antibiotics and Related Substances. XXI. The Synthesis of Deoxy and Chlorodeoxy Derivatives of Kanamycin

Abstract 1) Deoxykanamycin has been synthesized in a four-stage sequence beginning with kanamycin. Kanamycin has been converted to tetra-N-carbobenzoxykanamycin, and this transformed in turn to tetra-N-carbobenzoxy-mono-O-tosylkanamycin (or the corresponding nasyl derivative), to tetra-N-carbobenzoxy-deoxyiodokanamycin, and finally to deoxykanamycin. 2) The above nasyl derivative has been transformed via tetra-N-carbobenzoxy-chlorodeoxy-kanamycin to chlorodeoxy-kanamycin. 3) 6-O-(3-Amino-6-chloro-3,6-dideoxy-α-d-glucosyl)-deoxystreptamine hydrochloride has been obtained by the controlled acid-hydrolysis of chlorodeoxy-kanamycin. 4) The hydrogenolysis of tetra-N-carbobenzoxy-bromodeoxy-kanamycin has given deoxykanamycin. 5) It has been found that deoxykanamycin and chlorodeoxy-kanamycin are strongly antibacterial and that their antibiotic spectra are essentially similar to that of kanamycin.