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, two strategies were considered for the synthesis of 2,3-unsaturated O-glucosyl-1,2, 3-triazoles using Ferrier rearrangement.
Abstract: Two strategies were considered for the synthesis of 2,3-unsaturated O-glucosyl-1,2,3-triazoles. The first, involving reaction between tri-O-acetyl- d -glucal and triazole alcohols gave no stereoselectivity. A second strategy provided 2,3-unsaturated O-glycosides from glycals and alkynols through a Ferrier rearrangement; this method, employing montmorillonite K-10 doped with iron(III) chloride hexahydrate in dichloromethane afforded new glycosides in good to excellent yields within short times and with high α-stereoselectivities. Subsequently, the glucosides were coupled with 2-azido-1,4-naphthoquinone to produce a new series of 1,2,3-1H-triazolyl O-glucoside derivatives through a click reaction.
7 citations
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TL;DR: Stereoselectivity in the reaction of fully protected galactal derivatives was complete, although only a moderate increase in the syn epoxidation product was observed in 4,6- and 3,4-di-O-protected derivatives.
Abstract: 4,6-Di-O-protected glucal and allal derivatives react with MCPBA to afford manno- and allo-1-O-m-chlorobenzoate derivatives, respectively, as a result of a syn epoxidation directed by the allylic hydroxyl group, and consecutive ring-opening by m-ClBzOH. When glucal and allal derivatives are fully protected, initial epoxidation proceeds mainly anti to the allylic group to give, after ring-opening, the corresponding pyranosyl chlorobenzoates. Stereoselectivity in the reaction of fully protected galactal derivatives was complete, although only a moderate increase in the syn epoxidation product was observed in 4,6- and 3,4-di-O-protected derivatives. 1-O-m-Chlorobenzoate 18 was selectively protected and activated as donor in the synthesis of disaccharide 21.
7 citations
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TL;DR: In this paper, the stability of 3-and 4-hydroxyproline glycosides was evaluated using high-resolution n.m.r. spectral and chromatographic methods.
7 citations
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TL;DR: In this article, the mechanism of the cyclization reaction was probed using 1 H NMR and deuterium incorporation studies, which led to optimized stereoselectivity for the epoxide formation.
7 citations
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TL;DR: The mass spectra of O-acetyl and O-trimethylsilyl derivatives of d -glucal and d -xylal have been determined in this paper.
7 citations