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Stereocontrolled Conversion of Allylic Alcohols Into VicinalCis-Diols: New Syntheses of Methyl α-L-Digitoxoslde and Methyl 2-Deoxy-α-L-Fucoside

 

作者: HenryW. Pauls,   Bert Fraser-reid,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1985)
卷期: Volume 4, issue 1  

页码: 1-14

 

ISSN:0732-8303

 

年代: 1985

 

DOI:10.1080/07328308508062945

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

A synthetic process is outlined in which an allylic alcohol is converted into its primary urethane derivative, which is then subjected to iodonium ion induced cyclization to give a single iodo-carbonate. The carbonate is then deiodinated reductively and hydrolyzed to afford the vicinal diol. By use of this process the two title sugars have been prepared from methyl 2.3.6-trideoxv-α-L-ervthro-hex-2-enopvranoside and its α-L-threo counterpart.

 

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