Topic
Glucal
About: Glucal is a research topic. Over the lifetime, 590 publications have been published within this topic receiving 8960 citations. The topic is also known as: D-glucal.
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TL;DR: In this article, it was shown that tri-O -acetyl-d-glucal with thiophenol in the presence of BF 3 ·OEt 2 as catalyst gives the allylically rearranged S -phenyl 4,6-di- O-acetyl 2,3-dideoxy-1-thio-α- and β- d - erythro -hex-hex-2-enopyranosides as the main products.
Abstract: It is confirmed that tri- O -acetyl- d -glucal with thiophenol in the presence of BF 3 ·OEt 2 as catalyst gives the allylically rearranged S -phenyl 4,6-di- O -acetyl-2,3-dideoxy-1-thio-α- and β- d - erythro -hex-2-enopyranosides as the main products, and now demonstrated that the presence of catalytic proportions of water diverts the reaction in favour of the isomeric S -phenyl 4,6-di- O -acetyl-2-deoxy-3-phenylthio-1-thio- d - arabino - and - d - ribo -hexopyranosides. It is proposed that these products are formed from an intermediate enal.
14 citations
TL;DR: In this article, an intramolecular cycloaddition of the nitrone derived from the glucal produces stereospecifically the isoxazolidine 9 which may be reductively cleaved to afford functionalised aminotetrahydrofuran polyols such as 20 and 23.
14 citations
TL;DR: In this paper, a mixture of 3,4,6-tri-O-acetyl-D-glucal with carbon monoxide and hydrogen in the presence of dicobalt octacarbonyl was used to yield two epimeric anhydrodeoxyheptitols.
Abstract: 3,4,6-Tri-O-acetyl-D-glucal reacted with carbon monoxide and hydrogen in the presence of dicobalt octacarbonyl to yield a mixture of two epimeric anhydrodeoxyheptitols, namely, 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-manno-heptitol (I) and 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-gluco-heptitol (II). De-O-acetylation of the mixture, followed by chromatographic separation, yielded crystalline 2,6-anhydro-3-deoxy-D-manno-heptitol (III) and 2,6-anhydro-3-deoxy-D-gluco-heptitol (IV). Reaction of the mixture of heptitols (I) and (II) with p-bromobenzenesulfonyl chloride, followed by fractional crystallization of the brosylates, gave pure 4,5,7-tri-O-acetyl-2,6-anhydro-1-O-(p-bromophenylsulfonyl)-3-deoxy-D-gluco-heptitol (VII). The absolute configuration of (VII) has been previously established by X-ray crystallographic analysis. The absolute configuration of (III) was established by correlation with that of (VII). The conversion of compound (II) into various derivatives is described.Reaction of 3,4,6-tri-O-ac...
13 citations
13 citations
TL;DR: Following addition of N-iodosuccinimide to glycals, reductive hydrogenolysis and ring opening gave 2-deoxy-α-N-glycopeptides carrying a deaminated asparagine unit assumed to be of interest as potential inhibitors of the renin-angiotensi system.
13 citations