Process for preparing synthetic intermediates of 2-alkynyladenos

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 276, 536 2762, C07H 19067

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054592542

ABSTRACT:
The present invention relates to a novel compound represented by the following formula [I] which is useful as a synthetic intermediate of a 2-alkynyladenosine.
The present invention also relates to a process for producing the compound and a process for producing a 2-alkynyladenosine [IV] by way of the compound.
Further, the present invention relates to a 2-alkynyladenosine derivative represented by the following formula [V] having excellent storage stability and, to a method of storing the 2-alkynyladenosine in the form of that derivative. ##STR1## [I] A=a leaving group, [II] A=NH.sub.2,
[V] A=NHR.sup.4,
wherein R.sup.1 through R.sup.4 represent a hydrogen atom or a protective group, and n denotes an integer of 1 to 15, provided that R.sup.1 through R.sup.4 do not represent a hydrogen atom simultaneously.

REFERENCES:
patent: 4956345 (1990-09-01), Miyasaka et al.
Matsuda et al.(I), "Synthesis and Pharmacological Activities of 2-Alkynyl- and 2-Alkenyladenine Nucleosides," Nucleic Acids Research Symposium Series, No. 16, IRL Press Ltd., Oxford, England, 1985, see pp. 97-100.
Matsuda et al. (II), "Introduction of Carbon Substituents at C-2 Position of Purine Nucleosides," Nucleic Acids Research Symposium Series, No. 12, IRL Press Ltd., Oxford, England, 1983, see pp. 5-8.
Matsuda et al. (III), "Palladium-Catalyzed Cross-Coupling of 2-Iodoadenosine With Therminal Alkynes: Synthesis and Biological Activities of 2-Alkynyladenosines," Chem. Phar. Bull., 33(4), 19766-1769 (1985).
Kochetkov et al., Organic Chemistry of Nucleic Acids, Part B, Plenum Press, New York, 1972, see p. 333.
Nair et al., "Copper Mediated Reactions in Nucleoside Synthesis," Tett. Lett., 31(6), 807-810 (1990).
J. R. M. Scott, Supplementary European Search Report, European Patent Office, Dec. 13, 1991, Appl. No. EP 90 90 9403.

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