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Synthesis of Specifically Deuteriated Derivatives of D-Galactose and D-Galactosamine

Gupta, Dipti and Surolia, Avadhesha (1992) Synthesis of Specifically Deuteriated Derivatives of D-Galactose and D-Galactosamine. In: Journal of Carbohydrate Chemistry, 11 (2). pp. 171-182.

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Simple and convenient methods for introducing deuterium label at C-3 and C-6 position of N-acetyl-D-galactosamine and D-galactose, respectively, are described. For the synthesis of 2-acetamido-2-deoxy-D-3-[2H] galactopyranose, benzyl 2-acetamido-2-deoxy-4,6-O-benzylidene-agr-D-galactopyranoside was oxidized with dimethyl sulfoxide- acetic anhydride and the product was reduced with sodium borodeuteride to introduce the deuterium at C-3. After benzylidene reduction, the mixture was subjected to hydrogenolysis and purified by column chromatography. 1,2:3,4-di-O-isopropylidene-agr-D-galactopyranoside was oxidized followed by reduction with sodium borodeuteride and deprotection to yield D-6-[2H] galactose.

Item Type: Journal Article
Publication: Journal of Carbohydrate Chemistry
Publisher: Taylor and Francis Group
Additional Information: Copyright of this article belongs to Taylor and Francis Group.
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited: 31 Dec 2009 06:14
Last Modified: 31 Dec 2009 06:14
URI: http://eprints.iisc.ac.in/id/eprint/24677

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