Process for producing acyclic nucleosides and process for separa

Details Process for producing acyclic nucleosides and process for separa Process for producing acyclic nucleosides and process for separa

1994-03-18

1998-08-11

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen bonded directly to ring carbon of the purine ring...

544243, 544244, 544277, 544311, 544312, 544314, 544316, 544317, 544318, C07D47318, C07D47334, C07D47316, C07D47330

Patent

active

057928681

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.
Herein is also disclosed an industrially favorable method for the separation of 9-substituted purine nucleosides which are important intermediates for the synthesis of acyclic nucleosides such as acyclovir, ganciclovir, and the like from ribonucleosides, which method comprises crystallizing only the 9-isomer from a solution or suspension containing both a 9-substituted purine nucleoside and a 7-substituted purine nucleoside by cooling the solution or/and by adding a crystallizing solvent thereto.

REFERENCES:
patent: 4199574 (1980-04-01), Schaeffer
patent: 4835104 (1989-05-01), Yokozeki et al.
patent: 5310895 (1994-05-01), Shiragami et al.
patent: 5336770 (1994-08-01), Shiragami
Nucleosides & Nucleotides, vol. 6, No. 1 and 2, pp. 385-386, 1987, J. Boryski, et al., "Transglycosylation of Guanine Nucleosides".
Nucleosides & Nucleotides, vol. 8, No. 4, pp. 529-536, 1989, J. Boryski, et al., "Application of the Transpurination Reaction to Synthesis of Acyclic Guanosine Nucleosides".
Database WPIL, Derwent Publications Ltd., AN-86-012206, abstract of SU-A-961 354, Aug. 7, 1985.
"Conciol Chemical & Technical Dictionary" (4th Enlarged Edition), Bennett, (1986), p. 23.
"Hawleg Condensed Chemical Dictionary" (12th Edition) Lewis, (1993) p. 21.
Boryski, Nucleosides and Nucleotides 6, 385(1987).
Boryski, Nucleosides and Nucleotides 8, 529(1989).

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