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DOI: 10.1039/A707193K (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 941-946

Novel synthesis of purine acyclonucleosides possessing a chiral 9-hydroxyalkyl group by sugar modification of 9-D-ribitylpurines

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Kosaku Hirota, Yasunari Monguchi, Hironao Sajiki, Magoichi Sako and Yukio Kitade

Abstract

A novel approach to the synthesis of purine acyclonucleosides having chiral carbons in the N9-hydroxyalkyl chain was achieved by using 9-(2,3-O-isopropylidene-D-ribityl)purines 1, which are readily prepared from commercially available purine nucleosides. 9-[(2S,3R)-2,3,4-Trihydroxybutyl]purines 4a and 4b, 9-[(2S,3S)-2,3,4-trihydroxybutyl]purines 6a and 6b, L-eritadenine 8, and its analogue 11 are conveniently synthesized via key intermediates, (2S,3S[hair space])-2,3-isopropylidenedioxy-4-(purin-9-yl)butanals 2 prepared by NaIO4 oxidation of diols 1.

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