This article presents a novel catalytic method by combining phase-transfer catalyst, benzyltriethylammonium chloride, with 4-dimethylaminopyridine for the syntheses of glycosyl esters from substituted phenoxyaeetie ac...This article presents a novel catalytic method by combining phase-transfer catalyst, benzyltriethylammonium chloride, with 4-dimethylaminopyridine for the syntheses of glycosyl esters from substituted phenoxyaeetie acids and the peracetate of α-D-l-bromosugars to produee eight novel β-glyeosyl esters in high yields. The struetures of the syn-thesized eompounds were established by IR, MS, ^1H NMR, and ^13C NMR speetra and elemental analyses.展开更多
Despite the significant progress in carbohydrate chemistry,there remains a pressing need for efficient and practical glycosylationmethods using simple glycosyl donors and with high atom economy.Herein,a new protocol f...Despite the significant progress in carbohydrate chemistry,there remains a pressing need for efficient and practical glycosylationmethods using simple glycosyl donors and with high atom economy.Herein,a new protocol for glycosylation with glycosyl chloride donors under palladium-catalyzed conditions is developed.PdII complex serves as a Lewis acid to promote the activation of glycosyl chloride for the formation of oxocarbeniumion intermediate.This new method is operationally simple,robust,and enables efficient synthesis of both O-and N-glycosides with a broad substrate scope.In particular,it offers an easy access to a range of N-ribonucleoside analogs.展开更多
基金Supported by the National Natural Science Foundation of China(No.20674023).
文摘This article presents a novel catalytic method by combining phase-transfer catalyst, benzyltriethylammonium chloride, with 4-dimethylaminopyridine for the syntheses of glycosyl esters from substituted phenoxyaeetie acids and the peracetate of α-D-l-bromosugars to produee eight novel β-glyeosyl esters in high yields. The struetures of the syn-thesized eompounds were established by IR, MS, ^1H NMR, and ^13C NMR speetra and elemental analyses.
基金G.C.thanks NSFC-91753124,NSFC-21672105,NSFC-21421062,and NSFC-21725204 for financial support for this work.
文摘Despite the significant progress in carbohydrate chemistry,there remains a pressing need for efficient and practical glycosylationmethods using simple glycosyl donors and with high atom economy.Herein,a new protocol for glycosylation with glycosyl chloride donors under palladium-catalyzed conditions is developed.PdII complex serves as a Lewis acid to promote the activation of glycosyl chloride for the formation of oxocarbeniumion intermediate.This new method is operationally simple,robust,and enables efficient synthesis of both O-and N-glycosides with a broad substrate scope.In particular,it offers an easy access to a range of N-ribonucleoside analogs.
