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: In this article, a highly stereoselective rapid C-glycosylation reaction was developed between glycal and unactivated alkynes in the presence of coppertriflate and ascorbic acid at low catalyst loading and at room temperature.
Abstract: A highly stereoselective rapid C-glycosylation reaction has been developed between glycal and unactivated alkynes in the presence of coppertriflate and ascorbic acid at low catalyst loading and at room temperature. A wide variety of glycals and aryl acetylenes participate in the reaction smoothly. TfOH generated during the reduction of Cu(OTf)2 by ascorbic acid may be the active catalyst for the glycosylation.
1 citations
1 citations
01 Jan 1991
TL;DR: In this article, three different reactions were selectively observed at the anomeric centre of appropriate glucopyranosyl derivatives when treated with samarium iodide(II): formation of glucal, reductive desulfonylation and formation of C-glycosides upon addition of cyclopentanone.
Abstract: Three different reactions were selectively observed at the anomeric centre of appropriate glucopyranosyl derivatives when treated with samarium iodide(II):formation of glucal,reductive desulfonylation and formation of C-glycosides upon addition of cyclopentanone
1 citations
TL;DR: Nucleophile displacement of the tosylate of 4 with nucleobase in the presence of NaH/DMF followed by deprotection gave the desired 1,2-unsaturated pyranosylphosphonates 7a-c.
Abstract: Ferrier rearrangement of 3,4,6-tri-O-acetyl-D-glucal (1) in the presence of triethylphosphite afforded the 2,3-unsaturated pyranose 2. Deacetylation and simultaneous migration of the double bond to 1,2-position in the sugar moiety was achieved by stirring in sodium ethoxide. Tosylation with one equivalent of tosyl chloride afforded 4. Nucleophile displacement of the tosylate of 4 with nucleobase in the presence of NaH/DMF followed by deprotection gave the desired 1,2-unsaturated pyranosylphosphonates 7a-c.
1 citations
TL;DR: In this article, a mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described, which employs 1 mol % of an air and moisture-tolerant rhenium−oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-α-glycosides.
Abstract: A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium−oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-α-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.
1 citations