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.
TL;DR: In contrast with the precedent reports described in peracetyl and perbenzyl-D-glucal, chlorination of 3-O-acetyl- and 3-deoxy-4-6-Obenzylonidene-Dglucalin in carbon tetrachloride predominantly occurred from the β-side to give the β -D-manno and β-Darabino adducts, respectively.
Abstract: In contrast with the precedent reports described in peracetyl-and perbenzyl-D-glucal, chlorination of 3-O-acetyl- and 3-deoxy-4,6-O-benzylidene-D-glucal in carbon tetrachloride predominantly occurred from the β-side to give the β-D-manno and β-D-arabino adducts, respectively.
TL;DR: In this article, a one-pot transformation of d-glucal in the presence of nucleophiles leads to the formation of racemic α-substituted α-hydroxymethyl furfuryl derivatives, versatile synthons for biologically active molecules.
Abstract: Lewis acid mediated one-pot transformation of d-glucal in the presence of nucleophiles leads to the formation of racemic α-substituted α-hydroxymethyl furfuryl derivatives, versatile synthons for biologically active molecules. Transformations using O-, S-, C-, and N-nucleophiles could be achieved readily under mild and scalable conditions. Indium triflate proved to be the catalyst of choice in terms of conversion and regioselectivity.
TL;DR: In this paper, reaction of the ArSCl adducts formed in situ from the protected glucals with carbon nucleophiles in the presence of SnCl4 is proposed as a novel route for a stereoselective synthesis of various C-β-D-glucosides.
Abstract: Reaction of the ArSCl adducts formed in situ from the protected glucals with carbon nucleophiles in the presence of SnCl4 is proposed as a novel route for a stereoselective synthesis of various C-β-D-glucosides.