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 paper, a convenient approach to enantiomerically pure 4-hydroxymethyl-3-phenoxy-2-azetidinone has been carried out using the easily available aldehyde 5 as chiral starting material.
Abstract: A convenient approach to enantiomerically pure 4-hydroxymethyl- 3-phenoxy-2-azetidinone has been carried out using the easily available aldehyde 5 as chiral starting material.
2 citations
Patent•
04 Apr 1995
TL;DR: An enzymatic process for the preparation of galactosyl β 1,3 glycal disaccharides such as Gal beta 1, 3Glucal, an intermediate useful in Lea preparation and an inhibitor of beta -galactosidase was disclosed in this paper.
Abstract: An enzymatic process is disclosed for the preparation of galactosyl beta 1,3glycal disaccharides such as Gal beta 1,3Glucal, an intermediate useful in Lea preparation and an inhibitor of beta -galactosidase. The process utilizes beta -galactosidase, an enzyme usually used for bond breaking, to form a bond between a galactoside and a glucal such as glycal, a 6-O-C1-C6 acylglucal or 6-O-C1-C6 acetylgalactal.
2 citations
TL;DR: Sulfuric acid immobilized on silica gel (H2SO4-SiO2) was used as an efficient and convenient promoter for Ferrier-type rearrangement of 3,4,6-tri-O-benzyl-dglucal in CH2Cl2 as mentioned in this paper.
Abstract: Sulfuric acid immobilized on silica gel (H2SO4-SiO2) was used as an efficient and convenient promoter for Ferrier-type rearrangement of 3,4,6-tri-O-benzyl-d-glucal in CH2Cl2, which is a difficult donor for this type of reaction. The acceptors include primary alcohols, secondary alcohols, pentanol, halogenated alcohol, sterols, thiol, and 2-naphthol. Thus, 2,3-unsaturated glycosides were obtained rapidly ( 62%) in good α-selectivity (α/β>4.2:1) under mild conditions.
1 citations
TL;DR: A tinglucal tributyl and triflate derived from isolevoglucosenone (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1] undergo the carbonylative Stille condensation under special conditions requiring AsPh3, LiCl, and powdered charcoal as co-catalysts to give a cross-conjugated dienone 6 in which the bicyclic alkene moiety is more reactive than the glucal alk
Abstract: A tinglucal tributyl[4,6-O-bis(t-butyl)silylidene-3-O-tris(isopropyl)silyl]tin 7 and a triflate derived from isolevoglucosenone (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate 10 undergo the carbonylative Stille condensation under special conditions requiring AsPh3, LiCl, and powdered charcoal as co-catalysts to give a cross-conjugated dienone 6 in which the bicyclic alkene moiety is more reactive than the glucal alkene moiety. This allows the regio- and stereoselective hydrogenation of the bicyclic alkene moiety giving an enone 21 that can be reduced stereoselectively to an allylic alcohol 22. Hydroboration of the glucal and bicyclic acetal opening generates a C(1-->4) linked disaccharide 25 in which a protected form of beta-D-glucopyranose is attached at position C(4) of a alpha-D-3-deoxy-ribo-hexopyranoside derivative via a (S)-hydroxymethano linker. (C) 2004 Elsevier Ltd. All rights reserved.
1 citations
TL;DR: A stable furanoid glucal, 3-O-benzyl-1,2-dideoxy-5,6-Oisopropylidene-d-arabino-hex-1-enofuranose (BIF) was synthesized, and the equilibrium association constant K for the charge-transfer complex formation with maleic anhydride in CDCl3 at 25°C was 0.131 mol−1 as determined by 13C NMR as discussed by the authors.
Abstract: A stable furanoid glucal, 3-O-benzyl-1,2-dideoxy-5,6-O-isopropylidene-d-arabino-hex-1-enofuranose (BIF) was synthesized, and the equilibrium association constant K for the charge-transfer complex formation with maleic anhydride in CDCl3 at 25°C was 0.131 mol−1 as determined by 13C NMR. BIF copolymerized with maleic anhydride almost alternatingly, AIBN being used as the initiator. Other electron accepting monomers such as N-phenylmaleimide and acrylonitrile also copolymerized with BIF. Terpolymerization of BIF-maleic anhydride-acrylonitrile gave the copolymer containing BIF residues.
1 citations