Process for the deoxygenation of nucleosides

Details Process for the deoxygenation of nucleosides Process for the deoxygenation of nucleosides

1991-03-07

1995-01-24

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 2721, 536 281, 536 282, C07H 1900

Patent

active

053843967

ABSTRACT:
An efficient process for the deoxygenation of 2'- and or 3'-hydroxyl groups of a nucleoside that includes reacting the hydroxyl group with 3-halopropionitrile or 2-nitroethylhalide and carbon disulfide in base to form a 2'- or 3'-(cyanoethylthio or nitroethylthio)thiocarbonyl, that is reductively eliminated and replaced with hydrogen. The deoxygenation process can be used in a wide variety of nucleoside syntheses that require the elimination of the 2'- or 3'-hydroxyl groups, including the preparation of 3'-substituted-2',3'-dideoxynucleosides such as 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine.

REFERENCES:
patent: 3282921 (0000-01-01), Verheyden et al.
patent: 3687931 (0000-01-01), Verheyden et al.
patent: 3755295 (0000-01-01), Verheyden et al.
patent: 3775397 (0000-01-01), Etzold et al.
patent: 4071680 (0000-01-01), Cook
patent: 4078139 (1978-03-01), Barton et al.
patent: 4230698 (0000-01-01), Bobek et al.
patent: 4604382 (0000-01-01), Lin et al.
patent: 4788181 (1988-11-01), Driscoll et al.
patent: 4904770 (0000-01-01), Starrett, Jr. et al.
patent: 4921950 (0000-01-01), Wilson
Chu et al., J. Org. Chem., v. 54, pp. 217-2225, (1989).
Anzai, et al., Agri. Biol. Chem. 37(2), 345 (1973).
Barrett, et al., J.C.S. Chem. Comm. 866 (1977).
Barrett, et al., J.C.S. Perkin I 2378 (1979).
Classon, et al., Acta Chemica Scandinavica B36, 251 (1982).
Colla, et al., Eur. J. Med. Chem.--Chim. Ther. 20(4), 295 (1985).
Chem. Abstract 101:192378c (1984).
Chem. Abstract 96:69346s (1982).
Chem. Abstract 105:227205f (1986).
Dyatkina, Sovie J. Biorg. Chem. 12, 563 (1986).
Heredewijn, et al., J. Med. Chem. 30, 1270 (1987).
Horton, et al., J. Org. Chem. 35, 10 (1970).
Horowitz, et al., J. Am. Chem. Soc. 86, 1896 (1964).
Horowitz , et al., J. Org. Chem. 29, 2076 (1984).
Horowitz, et al., J. Org. Chem. 31, 205 (1966).
Horowitz, et al., J. Org. Chem. 32, 817 (1967).
Horowitz, et al., Tet. Letters 1343 (1966).
Jain, et al., J. Org. Chem. 39, 30 (1974).
Lin, et al., Biochem. Pharmacol. 36, 2713 (1987).
Lin, et al., J. Med. Chem. 30, 440 (1987).
Lin, et al., J. Med. Chem. 21(1), 109 (1978).
Lin, et al., J. Med. Chem. 26, 1691 (1983).
Lin, et al., J. Med. Chem. 26, 544 (1983).
Krenitsky, et al, J. Med. Chem. 26(6), 891 (1983).
McCarthy, et al., J. Am. Chem. Soc. 88, 1549 (1966).
Prisbe and Martin, Synthec Communications 15(5), 401, (1985).
Robins, et al., Tet. Letters 25, 367 (1984).
Russell, et al., J. Am. Chem. Soc., 95, 4025 (1973).
Tong, et al., J. Org. Chem. 30, 2854 (1965).
Webb, et al., Nucleosides and Nucleotides 7(2), 147 (1988).
Nakayama, et al., Nucleosides & Nucleotides, 1(2), 139-146 (1982).
Codington, et al., J. Am. Chem. Soc., 82 (1960).
Yung, et al., J. Am. Chem. Soc., 83, 3065 (1961).
Fox, et al., J. Am. Chem. Soc., 78 (1956).
Horton, et al. Carbohydrate Research, 48 (1976).
Holy, et al., Collection of the Czechslovak Chem. Commun., 39 (1974).
Paquette, et al., J. Org. Chem., 56(3), 912 (1991).

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