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

Abstract

The key intermediate 1,2:5,6-di- O-isopropylidene-3-deoxy-3β-allyl-α- d-glucofuranose ( 8) could be conveniently prepared through radical induced allyl substitution at C-3 of appropriate 1,2:5,6-di- O-isopropylidene-α- 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 diastereomeric isoxazolidinocyclopentane derivative 20 was similarly converted to carbanucleoside 22.