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Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3,5-bishydroxymethyl cyclopentanol from D-glucose

Roy, B.G., Maity, J.K., Drew, M.G.B., Achari, B. and Mandal, S.B. (2006) Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3,5-bishydroxymethyl cyclopentanol from D-glucose. Tetrahedron Letters, 47 (50). pp. 8821-8825. ISSN 0040-4039

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To link to this item DOI: 10.1016/j.tetlet.2006.10.070

Abstract/Summary

The key intermediate 1,2:5,6-di-O-isopropylidene-3-deoxy-3 beta-allyl-alpha-D-glucofuranose (8) could be conveniently prepared through radical induced allyl substitution at C-3 of appropriate 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose derivatives (7a,b) and used to synthesize enantiomeric bishydroxymethyl aminocyclopentanols 13 and 19 by the application of a 1,3-dipolar nitrone cycloaddition reaction involving the C-5 or C-1 aldehyde functionality. The products were subsequently transformed into carbanucleoside enantiomers 15 and 21. The diastercomeric isoxazolidinocyclopentane derivative 20 was similarly converted to carbanucleoside 22. (c) 2006 Elsevier Ltd. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11591
Uncontrolled Keywords:nitrone cycloaddition reaction, synthesis, carbanucleosides, enantiomers, D-glucose , NITRONE CYCLOADDITION REACTION, ANTI-HIV ACTIVITY, CARBOCYCLIC NUCLEOSIDES, CLOSING METATHESIS, ANALOGS, PRECURSORS, SPIRONUCLEOSIDES, DERIVATIVES, POTENT, RINGS

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