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• W2056551799 abstract "Both anomers of O-protected 1-thio-d-gluco- and -d-mannopyranoses were selected to provide the substrates for developing a smooth and general methodology that gives access to anomeric glycosulfoxides. The behavior of the corresponding β-d-galactopyran derivatives was also investigated. 2-{1-[(2,3,4,6-Tetra-O-acetyl-β-d-glucopyranosyl)sulfinyl](1-methyl)ethyl}malonic acid diethyl esters 4 were thermolyzed in refluxing dichloromethane for generating 2,3,4,6-tetra-O-acetyl-β-d-glucopyranose-1-sulfenic acid (8), in the presence of 2-propynyl β-d-glucopyranoside tetraacetate (32). The syn-addition of transient 8 onto the triple bond of 32 furnished 2-[(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)sulfonyl]-2-propenyl β-d-glucopyranoside tetraacetate (34), after m-CPBA oxidation of the corresponding sulfinyl epimeric mixture 33. This synthetic pathway appears particularly attractive since it represents an example of a mild and versatile approach to thiodisaccharides of foreseeably significant biological behavior. Various carbohydrate-derived sulfenic acids, different in glycosyl moiety and sulfenic function positioning, and various alkynylated carbohydrates can be adopted as combining units in the synthesis of alkene-linked multivalent thiosaccharides." @default.
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• W2056551799 date "2005-08-02" @default.
• W2056551799 modified "2023-09-27" @default.
• W2056551799 title "Sulfenic Acids in the Carbohydrate Field. An Example of Straightforward Access to Novel Multivalent Thiosaccharides" @default.
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• W2056551799 doi "https://doi.org/10.1021/jo0510991" @default.
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