Synthesis of dibekacin analogs containing 3-oxa- and 3-aza-2,3,4-trideoxy-D-glycero-hexopyranose.
6-O-(3-Oxa-2,3,4-trideoxy-alpha-D-glycero-hexopyranosyl) derivatives (10 and 17) of both 3',4'-dideoxyneamine and 5-epifluoro-5,3',4'-trideoxyneamine have been prepared by coupling ethyl 6-O-benzyl-3-oxa-2,3,4-trideoxy-1-thio-D-glycero-hexopyranoside (5) with suitable aglycons. The corresponding 3"-aza derivative (19) of dibekacin (6) was prepared by oxidation of 1,3,2',6'-tetra-N-tosyldibekacin (7) with Pb(OAc)4 followed by treatment with NH4OAc and reduction with NaBH3CN. Related ring-opening compounds (11 and 25) were also prepared.
Kuwahara
R
R
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Tsuchiya
T
T
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D003982:Dibekacin / Q000031:analogs & derivatives*; D006027:Glycosides / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis
D000900:Anti-Bacterial Agents; D006027:Glycosides; D009844:Oligosaccharides; D003982:Dibekacin