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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01 Jan 2000
TL;DR: Partial Table of Content CHEMICAL SYNTHESIS of GLYCOSIDES Trichloroacetimidates (R. Schmidt & K. Jung) Iterative Assembly of Glycals and Glycal Derivatives: The Synthesis of Glycosylated Natural Products and Complex Oligosaccharides (L. Williams, et al.)
Abstract: Partial Table of Content CHEMICAL SYNTHESIS OF GLYCOSIDES Trichloroacetimidates (R. Schmidt & K. - H. Jung) Iterative Assembly of Glycals and Glycal Derivatives: The Synthesis of Glycosylated Natural Products and Complex Oligosaccharides (L. Williams, et al.) Thioglycosides (S. Oscarson) Glycosylation Methods: Alkylations of Reducing Sugars (J. Tamura) Other Methods of Glycosylation (L. Panza & L. Lay) Glycolipid Synthesis (H. Ishida) Special Problems in Glycosylation Reactions: 2 - Deoxy Sugars (A. Veyrieres) Orthogonal Strategy in Oligosaccharide Synthesis (O. Kanie) Intramolecular Glycosidation Reactions (J. Madsen & M. Bols) SYNTHESIS OF OLIGOSACCHARIDE MIMICS Saccharide - Peptide Hybrids (H. Wessel) Index.
4 citations
TL;DR: The direction of the nucleophilic addition appears to be governed by the configuration of the anomeric carbon with β-linked sugars, and a Felkin-Ahn selectivity can be mainly presumed.
4 citations
4 citations
TL;DR: The ability of 2'-alpha-C-carboxyalkyl nucleosides to undergo an unusual two-step stereocontrolled nucleobase exchange process has been investigated and it is shown that the pentofuranosyl gamma-lactone is a good substrate for nucleoside synthesis by the Vorbrüggen procedures and undergoes completely stereoselective ring opening with either pyrimidine or purine silylated nucleobases to give novel 2'-C
Abstract: The ability of 2′-α-C-carboxyalkyl nucleosides to undergo an unusual two-step stereocontrolled nucleobase exchange process has been investigated. Upon silylation a protected 2′-deoxy-2′-α-C-(carboxymethyl)uridine derivative can undergo intramolecular displacement of the uracil base, by the 2′-carboxylic acid group, to form a pentofuranosyl γ-lactone. Under identical conditions the homologous 2′-deoxy-2′-α-C-(carboxyethyl)uridine derivative does not yield the corresponding δ-lactone, but undergoes elimination of uracil to give the corresponding glycal. The pentofuranosyl γ-lactone is a good substrate for nucleoside synthesis by the Vorbruggen procedures and undergoes completely stereoselective ring opening with either pyrimidine or purine silylated nucleobases to give novel 2′-C-carboxymethyl β-nucleosides in moderate to high yield.
4 citations
TL;DR: In this paper, a series of alkyl-and aryllithium-based reagents were used to generate 2,3-unsaturated β-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivities.
Abstract: Epoxide 4 is generated in situ from d-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated β-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the β-glycoside. Other organometallic reagents demonstrate more complex behavior in their reactions with epoxide 4.
4 citations