Transglycosilation process for producing acyclic nucleosides

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen bonded directly to ring carbon of the purine ring...

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544277, C07D47318, C07B 4304

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053367707

ABSTRACT:
Herein is disclosed a novel and industrially advantageous process for synthesizing acyclic nucleosides such as acyclovir and ganciclovir from ribonucleosides, which process comprises adding an acid catalyst and an acid anhydride to a solution of a ribonucleoside such as guanosine and an ester derivative of an acyclic sugar, and heating the mixture, whereby a transglycosilation reaction takes place between the ribose moiety of the ribonucleoside and the ester derivative of the acyclic sugar.

REFERENCES:
patent: 4199574 (1980-04-01), Schaeffer
patent: 4835104 (1989-05-01), Yokozeki et al.
Nucleosides and Nucleotides, vol. 6, Nos. 1 and 2, 1987, pp. 385-386, J. Boryski, et al., "Transglycosylation of Guanine Nucleosides".
Nucleosides & Nucleotides, vol. 8, No. 4, 1989, pp. 529-536, J. Boryski, et al., "Application of the Transpurination Reaction to Synthesis of Acyclic Guanosine Analogues".
Database WPIL, Derwent Publications Ltd., AN 86-012206, SU-A-961 354, Aug. 7, 1985.

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