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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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Journal ArticleDOI
TL;DR: As part of a program to find new sialidases and determine their enzymatic specificity and catalytic activity, a library of 4-methylumbelliferyl sialic acid glycosides derivatised at the C-5 position were prepared from N-acetylneuraminic acid.
Abstract: As part of a program to find new sialidases and determine their enzymatic specificity and catalytic activity, a library of 4-methylumbelliferyl sialic acid glycosides derivatised at the C-5 position were prepared from N-acetylneuraminic acid. Both α- and β-4-methylumbelliferyl sialic acid glycosides were prepared in high yields and stereoselectivity. α-Anomers were accessed via reagent control by utilising additive CH3CN and TBAI, whereas the β-anomers were synthesised through a diastereoselective addition reaction of iodine and the aglycone to the corresponding glycal followed by reduction of the resulting 3-iodo compounds. Both anomer-oriented synthetic pathways allow for gram-scale stereoselective syntheses of the desired C-5 modified neuraminic acid derivatives for use as tools to quantify the enzymatic activity and substrate specificity of known sialidases, and potential detection and investigation of novel sialidases.
Journal ArticleDOI
TL;DR: Titanocene(III) chloride and zirconcene(III), a mild reagents for radical generation in organic synthesis, were used for the conversion of glycosyl halides to glycals in this article.
Abstract: Titanocene(III) chloride and zirconcene(III) chloride are effective and mild reagents for radical generation in organic synthesis. In carbohydrate chemistry, these species are useful for the conversion of glycosyl halides to glycals, and for the stereospecific preparation of C -glycosides. In all cases, the 1-glycosyl radical is an active intermediate, generated by reaction of carbohydrate substrates with the organometallic.
Journal ArticleDOI
TL;DR: In this paper, auranoid glycal was utilized as a starting material for the nucleoside derivatives with the aid of benzenesulfenyl chloride and showed high stereoselectivity.
Abstract: Furanoid glycal was utilized as a starting material for the nucleoside derivatives with the aid of benzenesulfenyl chloride. Condensation reaction with silylated nucleic bases was high in the presence of SnCl 4 . Electrophilic addition of benzenesulfenyl chloride to the glycal with substituent also proceeded in high stereoselectivity. Phenylthio-substituted nucleoside was used to convert 2',3'-dideoxynucleoside and 2',3'-didehydro-2',3'-dideoxynucleoside
Journal ArticleDOI
TL;DR: Azidohydroxylation of 1-carbamoyl, 1-methoxycarbonyl and 1-cyano substituted d-lyxo and d-arabino configured O-peracylated glycals was studied and the reaction conditions were optimized as discussed by the authors .
Journal ArticleDOI
TL;DR: In this article, a 1,2:5,6-di-O-Isopropylidene-α-d -glucofuranose can be used as a starting material for the stereoselective synthesis of a novel [1,3]dioxolan-4-yl ester by an acid catalyzed rearrangement reaction of an unusual furanoid glycal.
Abstract: 1,2:5,6-di-O-Isopropylidene-α- d -glucofuranose can be used as a starting material for the stereoselective synthesis of a novel [1,3]dioxolan-4-yl ester by an acid catalyzed rearrangement reaction of an unusual furanoid glycal.
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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202312
202211
202111
202011
20197
201819