Synthesis of kanamycin A analogs containing 6-amino-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranose.
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-alpha-D-glucopyranosyl)-2-deoxystreptamine (16). Deprotection and reduction of the azido group of the condensation products gave the title compounds.
Kuwahara
R
R
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Tsuchiya
T
T
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D007612:Kanamycin / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D000900:Anti-Bacterial Agents; D014312:Trisaccharides; D007612:Kanamycin