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Synthesis of cyclic phosphonate analogs of ribose and arabinose

TitleSynthesis of cyclic phosphonate analogs of ribose and arabinose
Publication TypeJournal Article
Year of Publication1997
AuthorsHarvey, TC, Simiand, C, Weiler, L, Withers, SG
JournalJOURNAL OF ORGANIC CHEMISTRY
Volume62
Pagination6722-6725
Date PublishedOCT 3
ISSN0022-3263
Abstract

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 P-31 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.

DOI10.1021/jo9706382