Glycal

About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.

Synthesis of C-D-E trisaccharide precursors of olivomycin A.

Abstract: Syntheses of functionalized C-D-E trisaccharide precusors of olivomycin A are reported. A stereoselective C-D β-glycosidation was accomplished by employing 2-deoxy-2-(phenylthio)-α-glucotrichloroacetimidate. The α-D-E glycosidic linkage was introduced by using 2-deoxy-2-iodo-α-glycosyl acetate donor as the glycosyl agent

Straightforward Synthesis of (1-->2)-Linked Pseudo Aza-C-disaccharides by the Novel Cycloaddition of Enantiopure Cyclic Nitrones to Glycals.

Abstract: The novel, highly stereoselective, intermolecular cycloaddition reaction of enantiopure cyclic nitrones 8 to 1,2-glycals 9 opens the way to a straightforward synthesis of a broad class of new (1→2)-linked pseudo aza-C-disaccharides 6, suitable substrates for selective inhibition of glycosidase enzymes. The cycloadditions occur with high stereocontrol, displaying preferential interaction between the bottom face of the glycal and the face of the nitrone anti to the substituent on C-3, with the reagents approaching in an exo fashion. The cycloadditions produced tricyclic isoxazolidines 7 that represent nonreducing pseudo aza-C-disaccharides stable to hydrolytic conditions. The target pseudo aza-disaccharides 6 were obtained by sequential deprotection of the hydroxyl groups and isoxazolidine ring-opening.