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A Simple Access to Carbocyclic Analogs of 2-Deoxy-d-Ribose Having the 3-Hydroxymethylene Moiety Replaced by Heteroatoms

 

作者: Karsten Schürrle,   Wolfgang Piepersberg,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1996)
卷期: Volume 15, issue 4  

页码: 435-447

 

ISSN:0732-8303

 

年代: 1996

 

DOI:10.1080/07328309608005664

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

(2S,4S)-1-O-Benzyl-2,5-di-O-mesyl-4-O-methoxymethylpentan-1,2,4,5-tetrol, a versatile precursor for subsequent cyclisations with bivalent nucleophiles, was obtained in five steps from the easily accessible (3S,5S)-3-hydroxy-5-hydroxymethyldihydrofuran-2(3H)-one. Using diso-dium phosphide in DMSO or disodium selenide in acetone-water, (2R,4S)-2-benzyloxymethyl-4-O-methoxymethylphospholane and (2R,4S)-2-benzyloxymethyl-4-O-methoxymethylselenolane were prepared. The phospholane was oxidized by oxygen (hydrogen peroxide) to give the analogous cyclic phospholane oxide (phosphinic acid) which was then transformed with benzyl bromide and alkali carbonate into the 1-benzyl phospholane oxide (phosphinic acid benzyl ester). All heterocyclic compounds sythesized, formally resemblecarba-2,3-dideoxy-d-giycero-pentofuranose, the carbocyclic analog of 2-deoxy-α-d-ribofuranose.

 

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