A simplified synthesis of 8-substituted purine nucleosides via lithiation of 6-chloro-9-(2,3-O-isopropylidene-.BETA.-D-ribofuranosyl)purine.

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Abstract
6-Chloro-9-(2, 3-O-isopropylidene-β-D-ribofuranosyl) purine (1) was found to be a suitable substrate for the preparation of C-8 substituted purine nucleosides. Thus, upon lithiation of 1 with LDA and successive reaction with various types of electrophiles, the C-8 substituted products were obtained. The C-6 chlorine atoms in these products were readily replaced by an amino group, a mercapto group, or hydrogen, providing a facile preparation of 8-substituted adenosines, 6-thioinosines, or nebularines.

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