Intermediates useful in a synthesis of 2-chloro-2'-deoxyadenosin

Details Intermediates useful in a synthesis of 2-chloro-2'-deoxyadenosin Intermediates useful in a synthesis of 2-chloro-2'-deoxyadenosin

1992-04-16

1993-05-04

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

514 46, C07H 19167, C07H 19173

Patent

active

052083276

ABSTRACT:
This invention relates to a novel process for preparing 2-chloro-2'-deoxyadenosine (2-CdA) having the following formula ##STR1## from a compound of the following formula ##STR2## The invention also relates to intermediates which are useful in preparing 2-CdA. The compound 2-CdA is useful as an antileukemic agent, i.e., in treating leukemias, such as hairy cell leukemia.

REFERENCES:
patent: 4760137 (1988-07-01), Robins et al.
Robins et al., "Smooth and Efficient Degradation of Secondary Alcohols. A General Procedure for the Conversion of Ribonucleosides to 2'-Deoxynucleosides," J. Am. Chem. Soc., 103, 932,933 (1981).
Nair et al.(I), "Modification of Nucleic Acid Bases via Radical Intermediates: Synthesis of Dihalogenated Purine Nucleosides," Synthesis, 1982, 670-672.
Barton et al., "A New Method for the Deoxygenation of Secondary Alcohols," J. Chem. Soc. Perkin I, 1975, 1574-1585.
Nair et al.(II), "Utility of Purinyl Radicals in the Synthesis of Base-Modified Nucleosides and Alkylpurines: 6-Amino Group Replacement by H, Cl, Br and I," J. Org. Chem., 45(20), 3969-3974 (1980).
Seto et al., "Biochemical Basis for Deoxyadenosine and 2-Chlorodeoxyadenosine Toxicity to Resting Human Lymphocytes," in Purine and Pyrimidine Metabolism in man V, Nyhan et al. (eds.), Plenum Publishing Corp., New York, N.Y., 1986.
Wright et al., "Convenient Synthesis of 2-Halo-2'-deoxyadenosines," J. Org. Chem., 52, 4617-4618 (1987).
Kazimierczuk et al., "Synthesis of 2'-Deoxytubercidin, 2'-Deoxyadenosine, and Related 2'-Deoxynucleosides via a Novel Direct Stereospecific Sodium Salt Glycosylation Procedure," J. Am. Chem. Soc., 106, 6379-6382 (1984).
Montgomery, "The Chemistry and Biology of Nucleosides of Purines and Ring Analogs," in Nucleosides, Nucleotides, and Their Biological Applications, Academic Press, Inc., 1983, New York, N.Y., pp. 19-46.

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