Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: The reaction of 3,4,6-tri-O-benzyl-D-glucal (2) with 3,3-dimethyldioxirane gives rise to the 2α,3α-oxirane with high stereoselection as mentioned in this paper.
Abstract: The reaction of 3,4,6-tri-O-benzyl-D-glucal (2) with 3,3-dimethyldioxirane gives rise to the 2α,3α-oxirane with high stereoselection. Reaction of this compound with various phenols under alkaline conditions affords aryl 2α-hydroxy-β-glycosides (3a-d). Oxidative coupling (I + ) of these compounds with glycals followed by deiodination gives rise to aryloxydisaccharides (6a and 6b). In addition, proton-mediated coupling of 3a and 3b with vancosamine-derived glycal 8 affords 10a and 10b, which simulate the aryloxy carbohydrate domain of vancomycin
84 citations
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TL;DR: Iodine(III)-mediated nitrenoid formation, interaction of this species with the glycal enol ether pi-system, and highly beta-stereoselective glycosylation occur in a one-pot process that requires no additional Lewis acid activation.
84 citations
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TL;DR: In this article, tri-O-acetyl-d-glucal 1 with various alcohols and phenols in the presence of InCl3/CH2Cl2 at ambient temperature gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields with short reaction times and good anomeric selectivity.
83 citations
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TL;DR: Monosubstituted isomerically pure indolopyrrolocarbazole precursors have been prepared via palladium-catalyzed asymmetric allylic alkylation methodology, employing both achiral cyclopentenyl electrophiles and chiral glycal derivatives.
83 citations