Process for preparation of 2-deoxy-2,2-difluoro-D-ribofuranosyl-

Details Process for preparation of 2-deoxy-2,2-difluoro-D-ribofuranosyl- Process for preparation of 2-deoxy-2,2-difluoro-D-ribofuranosyl-

1993-08-25

1995-06-13

Robinson, Douglas W.

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

Organic compounds

Carbohydrates or derivatives

536118, 536125, C07H 508, C07H 100, C07H 1914, C07H 1916

Patent

active

054244161

ABSTRACT:
A stereoselective process for preparing a .beta.-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-hydroxy protected-1-alkyl and aryl sulfonate intermediates by contacting an .alpha.-anomer enriched 2-deoxy-2,2-difluoro-D- ribofuranosyl-3,5-hydroxy protected-1-fluoroalkyl and fluoroaryl sulfonate with a conjugate anion of a sulfonic acid containing the desired alkyl or aryl sulfonate.

REFERENCES:
patent: 3282921 (1966-11-01), Verheyden et al.
patent: 4145531 (1979-03-01), Eckstein et al.
patent: 4211773 (1980-07-01), Lopez et al.
patent: 4526988 (1985-07-01), Hertel
patent: 4625020 (1986-11-01), Brundidge et al.
patent: 4751221 (1988-06-01), Watanabe et al.
patent: 4965374 (1990-10-01), Chou et al.
Watanabe et al., "Nucleosides. 110. Synthesis and Antiherpes Virus Activity of Some 2'-Fluoro-2'-deoxyarabinofuranosylpyrimidine Nucleosides," J. Medicinal Chem., 22(1), 21-24 (1979).
Hertel et al., "Synthesis of 2-Deoxy-2,2-difluoro-D-ribose and 2-Deoxy-2,2-difluoro-D-ribofuranosyl Nucleosides," J. Org. Chem., 53, 2406-2409 (1988).
Nishimura et al., "A New Synthetic Method of [for Making] Nucleosides," Chem. Pharm. Bull., 11(11), 1470-1472 (1963).
Nishimura et al., "Studies on Synthetic Nucleosides. IV. A New Synthetic Method of Pyrimidine and Purine Ribosides," Chem. Pharm. Bull., 12(2), 1471-1478 (1964).
Barton et al., Comprehensive Organic Chemistry, The Synthesis and Reactions of Organic Compounds, vol. 5, Biological Compounds, Pergamon Press, New York, 1979, 1979 & 22.2.3.1 (Condensation Reactions), see pp. 60-67.
Wittenburg, "Eine neue Synthese von Nucleosiden," Z. Chem., 4(8), 303-304 (1964).
Vorbruggen, et al., J. Org. Chem., 41, 2084 (1976).
Kazimierczuk, et al., J. Am. Chem. Soc., 106, 6379-82 (1984).
Seela, et al., Liebigs Ann. Chem., 895-901 (1989).
Reichman, et al., Carbohydr. Res., 42, 233 (1975).
Howell, et al., J. Org. Chem., 53, 85-88 (1988).
Davoll, et al., J. Am. Chem. Soc., 73, 1650 (1951).
Hilbert, et al., J. Am. Chem. Soc., 52, 2001 (1930).
Sanghvi, et al., Nucleosides & Nucleotides, 6(4), 761-774 (1987).
Koenigs, eta l., Berichete Dent. Chem. Gesselschaft, 34, 957-981.
Prystas, et al., Coll. Czech. Chem. Comm., 31, 3990-4001 (1966).
Hoffer, et al., Chem. Ber., 93, 2777-2781 (1960).
Wittenburg, et al., Chem. Ber., 101, 1095-1114 (1968).
Howard, et al., J. Am. Chem. Soc., 1052-1054 (1947).
Hertel, et al., Nucleosides & Nucleotides, 8(5&6), 951-955 (1989).
Hubbard, et al., Nucleic Acid Research, 12, 6827 (1984).

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