Synthesis of prumycin and related compounds.
Prumycin (1) and related compounds have been synthesized from benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-beta-D-glucofuranoside (4). Benzoylation of 4, followed by deisopropylidenation, gave benzyl 3-O-benzoyl-2-(benzyloxycarbonyl)amino-2-deoxy-beta-D-glucofuranoside (6), which was converted, via oxidative cleavage at C-5-C-6 and subsequent reduction, into the related benzyl beta-D-xylofuranoside derivative (7). Benzylation of 3-O-benzoyl-2-(benzyloxycarbonyl)-amino-2-deoxy-D-xylopyranose (8), derived from 7 by hydrolysis, afforded the corresponding DERIVATIVES (9,11) of beta-and alpha-D-xylopyranoside, and compound 7 as a minor product. Treatment of benzyl 3-O-benzoyl-2(benzyloxycarbonyl)amino-2-deoxy-4-O-mesyl-beta-D-xylopyranoside (10), formed by mesylation of 9, with sodium azide in N,N-dimethylformamide gave benzyl 4-azido-3-O-benzoyl-2-(benzyloxycarbonyl)amino-2,4-dideoxy-alpha-L-arabinopyranoside (13), which was debenzoylated to compound 14. Selective reduction of the azide group in 14, and condensation of the 4-amine with N-[N-benzyloxycarbonyl)-D-alaninoyloxy]succinimide, gave the corresponding derivative (15) of 1. Reductive removal of the protecting groups of 15 afforded 1. Prumycin analogs were also synthesized from compound 14. Evidence in support of the structures assigned to the new derivatives is presented.
D000617:Aminoglycosides / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000032:analysis; D008722:Methods; D008968:Molecular Conformation; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared
D000617:Aminoglycosides; D000935:Antifungal Agents; D002241:Carbohydrates