Syntheses of acyclic guanine 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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560236, C07D47318, E07B 4304

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056484895

ABSTRACT:
A method is provided for the synthesis of synthesis of acyclic purine nucleosides, particularly 9-(2-hydroxy-ethoxymethyl)-guanine (acyclovir) and 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine ("DHPG") where the N.sup.2,N.sup.9 -diprotected guanine is reacted with CH.sub.3 C(O)OCH.sub.2 O(CH.sub.2).sub.2)OC(O)CH.sub.3 or 2-acetoxymethoxy-1,3-diacetoxypropane, respectively, in the presence of a mixture of an acid and acetic anhydride, or in the presence of an acid, where the acid can be phosphoric acid or polyphosphoric acid.

REFERENCES:
patent: 5336770 (1994-08-01), Shiragami et al.
Acton, E.M. et al., "The Mercury Salt of 2-Acetamido-6-chloropurine," Synthetic Procedures in Nucleic Acid Chemistry 1968, 1, 25-27.
Boryski, J., et al., "Transglycosylation of Guanine Nucleosides," Nucleosides & Nucleotides, 6(1 & 2): 385-386 (1987).
Boryski, J., et al., "Application of the Transpurination Reaction to Synthesis of Acyclic Guanosine Analogues," Nucleosides & Nucleotides, 8(4):529-536 (1989).
Chen et al., "An Improved Synthesis of Acyclovir", Chemical Abstracts, 117:151269e (1992).
Field, A.K. et al., "9{[2-Hydroxyl-1-(hydroxymethyl)ethoxy]methyl}guanine: A selective inhibitor of herpes group virus replication," Proc. Natl. Acad. Sci.: USA, 1983, 80, 4139-4143.
Hakimelahi, G.H., et al., "Catalytic Effect of Tetrabutylammonium Fluoride in the Preparation of Secoribo-nucleosides," Helv. Chim. 1989, 72, 1495-1500.
Martin J.C. et al., "9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine: A New Potent and Selective Antiherpes Agent," J. Med. Chem. 1983, 26(5), 759-761.
Matsumoto, H. et al., "A Convenient Synthesis of 9-(2-Hydroxyethoxy-methyl)guanine (Acyclovir) and Related Compounds," Chem. Pharm. Bull. 1988, 36(3), 1153-1157.
Ogilivie, K.K. et al., "Biologically active acyclonucleoside analogues. II. The Synthesis of 9-[(2-hydroxy-1-(hydroxymethyl)ethoxy) methyl] guanine (BIOLF-62)," Can J. Chem 1982, 60, 3005-3010.
Schaeffer, H.J. et al., "9-(-Hydroxyethoxymethyl)guanine activity against viruses of the herpes group," Nature 1978 (London), 272, 583-585.
Zou et al., "High-yield regioselective synthesis of 9-glycosyl guanine nucleosides and analogues via coupling with 2-N-acetyl-6-O-diphenylcarbamoylguanine," Can J. Chem. 1987, 65, 1436-1437 .

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