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

 

作者: Dipti Gupta,   Avadhesha Surolia,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1992)
卷期: Volume 11, issue 2  

页码: 171-182

 

ISSN:0732-8303

 

年代: 1992

 

DOI:10.1080/07328309208017798

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

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-α-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-α-D-galactopyranoside was oxidized followed by reduction with sodium borodeuteride and deprotection to yield D-6-[2H] galactose.

 

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