Issue 5, 1998
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

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 )-2,3-isopropylidenedioxy-4-(purin-9-yl)butanals 2 prepared by NaIO4 oxidation of diols 1.

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Article information

DOI
https://doi.org/10.1039/A707193K
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1998, 941-946

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

K. Hirota, Y. Monguchi, H. Sajiki, M. Sako and Y. Kitade, J. Chem. Soc., Perkin Trans. 1, 1998, 941 DOI: 10.1039/A707193K

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