2,2-difluoro-3-carbamoyl ribose sulfonate compounds and process

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

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536 2711, 536 285, 536 2851, 514 29, C07H 504, C07H 506, C07H 19073

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055212948

ABSTRACT:
This invention provides novel 1-alkylsulfonyl-2,2-difluoro-3-carbamoyl ribose intermediates and intermediate nucleosides derived therefrom. The compounds are particularly useful in the preparation of 2'-deoxy-2',2'-difluoro-beta-cytidine and other beta anomer nucleosides which are antiviral and anticancer agents.

REFERENCES:
patent: 2949449 (1960-08-01), Hoffer
patent: 3575959 (1971-04-01), Shen et al.
patent: 3658786 (1972-04-01), Albrecht et al.
patent: 4526988 (1985-07-01), Hertel
patent: 4656260 (1987-04-01), Kato et al.
patent: 4760137 (1988-07-01), Robins et al.
patent: 4808614 (1989-02-01), Hertel
patent: 4904771 (1990-02-01), Katsunuma et al.
patent: 4954623 (1990-09-01), Nagarajan
patent: 4965374 (1990-10-01), Chou et al.
patent: 5070190 (1991-12-01), Lockhoff et al.
patent: 5216145 (1993-06-01), Raifeld
patent: 5371210 (1994-12-01), Chou
patent: 5424416 (1995-06-01), Jones
Okauchi et al., "Stereoselective Synthesis of .beta.-2-Deoxyribonucleosides from 1-O-Acetyl-3-O-[2-(methylsulfinyl)ethyl]-2-ribose," Chemistry Letters, 1989, 801-804.
Ichikawa et al., "Stereoselective .beta.-C- and .beta.-S-Glycosylation of 2-Deoxyribofuranose Derivatives Controlled by the 3-Hydroxy Protective Group," Bull. Chem. Soc. Japan, 62(3), 845-852 (1989).
Wierenga et al., "Stereochemical Control as a Function of Protecting-Group Participation in 2-Deoxy-D-erythro-pentofuranosyl Nucleosides," Carbohydrate Res., 90, 41-52 (1981).
Plusquellec et al., "Sugar Chemistry Without Protecting Groups: A Regioselective Addition of the Primary Hydroxyl of Monosaccharides to Alkylisocyanates," Tetrahedron Letters, 28(36), 4165-4168 (1987).
Wolfrom et al., "Crystalline Phenylurethans (Carbanilates) of Sugar Glycosides", J. Am. Chem. Soc., 62, 1151-1153 (1940).
C. B. Reese, "Protection of Alcoholic Hydroxyl Groups and Glycol Systems," Ch. 3 in Protective Groups in Organic Chemistry, Plenum Press, New York, NY, 1973, pp. 95-143.
Goodman (I), "Chemical Syntheses and Transformations of Nucleosides. Synthesis of Nucleosides," Ch. 2, Sect. II in Basic Principles in Nucleic Acid Chemistry, vol. 1, Ts'O et al. (eds.), Academic Press, New York, NY, 1974, pp. 95-128, particularly pp. 104-105.
Goodman (II), "Chemical Syntheses and Transformations of Nucleosides. Chemical Transformations That Involve both the Sugar and the Heterocyclic Base; Pyrimidine Cyclonucleosides," Ch. 2, Sect. V, Part 2 in Basic Principles in Nucleic Acid Chemistry, vol. 1, Ts'O et al. (eds.), Academic Press, New York, NY, 1974, pp. 177-190.
Protective Groups in Organic Synthesis, Greene, John Wiley & Sons, N.Y., Chapter 2 (1981), pp. 10-86.

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