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Synthetic Approach to Kdo Glycosides Via Exo-Glycal Epoxides and Rationalization of the Stereo Chemical Outcome

 

作者: Luigi Lay,   Francesco Nicotra,   Luigi Panza,   Giovanni Russo,   Guido Sello,  

 

期刊: Journal of Carbohydrate Chemistry  （Taylor Available online 1998）
卷期: Volume 17, issue 8  

页码: 1269-1281

 

ISSN:0732-8303

 

年代: 1998

 

DOI:10.1080/07328309808001899

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

The use of epoxides obtained by dimethyldioxirane epoxidation of 2,3-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol as glycosyl donors is described. This method offers a simple and stereoselective access to precursors of Kdo glycosides. The stereochemical outcome of the reaction is rationalized by means of semiempirical calculations of the transition states leading to glycosides formation.

 

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