Synthesis of 1-N-(D-threo- and racemic erythro-3-amino-2-hydroxybutanoyl)-2',3'-dideoxykanamycin A.
1-N-(D-Threo-3-amino-2-hydroxybutanoyl)-2',3'-dideoxykanamycin+ ++ A has been prepared by coupling of 3,6'-bis(N-benzyloxycarbonyl)-2',3'-dideoxy-3"-N-(trifluoroacetyl)kanamy cin A with D-threo-3-azido-2-hydroxybutanoic acid. A diastereomeric mixture of the erythro analog has also been prepared by use of racemic erythro-3-azido-2-hydroxybutanoic acid. Synthesis of the D-threo- and racemic erythro-3-amino-2-hydroxybutanoic acids has been described.
Umemura
E
E
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Tsuchiya
T
T
Umezawa
S
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007612:Kanamycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; C056045:1-N-(3-amino-2-hydroxybutanoyl)-2',3'-dideoxykanamycin A; D007612:Kanamycin