Preparation of benzyl 2-benzyloxycarbonylamino-4-dichloroacetamido-2,4-dideoxy-alpha- D-xylopyranoside, substrate for the synthesis of the heterocyclic analogue of chloromycetin.
The paper describes the eleven stage synthesis of the derivative (XI) of 2,4-diamino-2,4-dideoxy-D-xylose, containing amino groups selectively substituted by two different acyls. The initial substrate was L-arabinose. The compound obtained, after removing the blocking groups, constitutes a semiproduct for the synthesis of the pyrrole analogue of chloromycetin by the Knorr method.
Krajewska
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D
Department of Organic Chemistry, Medical Academy of Białystok.
Rózański
A
A
D000215:Acylation; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001089:Arabinose / Q000031:analogs & derivatives / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D002701:Chloramphenicol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002855:Chromatography, Thin Layer; D003837:Deoxy Sugars / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared; D014994:Xylose / Q000031:analogs & derivatives / Q000737:chemistry
C112319:2,4-diamino-2,4-dideoxyxylose; D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D003837:Deoxy Sugars; D011758:Pyrroles; C112320:benzyl 2-benzyloxycarbonylamino-4-dichloroacetamido-2,4-dideoxyxylopyranoside; D002701:Chloramphenicol; D014994:Xylose; D001089:Arabinose