uridine-diphosphate-n-acetylmuramic-acid and trichloroacetamide

(2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl trichloroacetimidate (3) and its polymer-supported reagent 4 can be successfully applied to a one-pot protection-glycosylation reaction to form the disaccharide derivative 7 d for the synthesis of lipid II analogues. The temporary protecting group or linker at the C-6 position and N-Troc protecting group of 7 d can be cleaved simultaneously through a reductive condition. Overall yields of syntheses of lipid II (1) and neryl-lipid II N(ε)-dansylthiourea are significantly improved by using the described methods.

Topics: Acetamides; Chloroacetates; Disaccharides; Glycosylation; Hydrocarbons, Chlorinated; Methyl Ethers; Peptidoglycan Glycosyltransferase; Polymers; Uridine Diphosphate N-Acetylmuramic Acid