Synthesis of Cyclic Phosphonate Analogs of Ribose and Arabinose

The cyclic phosphonates of ribose and arabinose (phostones) 10−13 were synthesized by a Lewis acid-catalyzed addition of trimethyl phosphite to the partially protected d-threose 7 to give the acyclic phosphonates 8 and 9. This Abramov reaction was moderately stereoselective (3:1). A base-catalyzed c...

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Bibliographic Details
Published in:Journal of organic chemistry 1997-10, Vol.62 (20), p.6722-6725
Main Authors: Harvey, Thomas C, Weiler, Larry, Withers, Stephen G
Format: Article
Language:English
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Summary:The cyclic phosphonates of ribose and arabinose (phostones) 10−13 were synthesized by a Lewis acid-catalyzed addition of trimethyl phosphite to the partially protected d-threose 7 to give the acyclic phosphonates 8 and 9. This Abramov reaction was moderately stereoselective (3:1). A base-catalyzed cyclization of the mixture of 8 and 9 gave the four isomeric phosphonates 10−13. Two of the isomers, 10 and 11, could be crystallized from the reaction mixture. The stereochemistries of 11 and 16, the tribenzyl ether from 10, were proven by X-ray crystallography, and the stereochemistries of the other isomers and derivatives were determined by 31P NMR chemical shift data. The X-ray data and solution NMR data indicate that these phostones and their derivatives exist exclusively in a chair conformation.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9706382