Synthesis of kanamycin A analogs containing 6-amino-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranose

Article abstract of DOI:10.1016/0008-6215(96)00051-1

6-Azido-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranoses were synthesized in five steps from (2S)- and (2R)-1,2-O-isopropylideneglycerols, respectively. After conversion into the corresponding ethyl 1-thioglycosides, each was condensed with a protected derivative of 6-O-(3-amino-3-deoxy-α-D-glucopyranosyl)-2-deoxystreptamine (16). Deprotection and reduction of the azido group of the condensation products gave the title compounds.