Novobiocin-related compounds: synthesis of 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl D-glycopyranosides by the trichloroacetimidate methodology.
A general stereoselective method for the synthesis of 4-deoxynovobiocin-related glycosides is described. 3-Benzoylamino-2H-1-benzopyran-7-yl 2,3,4,6-tetra-O-acetyl-D-glycopyranosides of glucose, galactose and mannose were synthesised from appropriate O-glycosyltrichloroacetimidates and N-(7-hydroxy-2-oxo-2H-1-benzopyran-3-yl)benzamides in boiling methylene chloride in the presence of boron trifluoride etherate. Heating of these products in a mixture of triethylamine and methanol gave the corresponding deprotected 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl beta-D-glycopyranosides.
Jeselnik
M
M
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Slovenia.
Plavec
J
J
Polanc
S
S
Kocevar
M
M
D000081:Acetamides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D001578:Benzopyrans / Q000737:chemistry; D062845:Chloroacetates; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis; D009675:Novobiocin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D000900:Anti-Bacterial Agents; D001578:Benzopyrans; D062845:Chloroacetates; D006027:Glycosides; D009005:Monosaccharides; D009675:Novobiocin; D014238:Trichloroacetic Acid; C009528:trichloroacetamide