Deoxygenation of cis vicinal diols to make didehydro dideoxy nuc

Details Deoxygenation of cis vicinal diols to make didehydro dideoxy nuc Deoxygenation of cis vicinal diols to make didehydro dideoxy nuc

1993-02-03

1995-04-25

Rollins, John W.

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

Organic compounds

Carbohydrates or derivatives

536 2762, 536 282, 536 285, 536 2853, 568704, C07H 19073, C07H 19173

Patent

active

054100330

ABSTRACT:
Cis vicinal diols are converted to olefins using tellurides or selenide reagents. The diol is reacted to convert the hydroxyl groups into good leaving groups for nucleophilic substitution. Alkyl and aryl sulfonate groups such as mesylate or tosylate are preferred. The product is then reacted with a source of Te.sup.2- or Se.sup.2- ions, preferably an alkali metal telluride or selenide, to form the desired olefin. The process is particularly useful for generating 2',3'-unsaturation in the sugar moiety of nucleosides. Novel intermediate mesylate, tosylate and olefin derivatives of nucleosides are also provided.

REFERENCES:
patent: 4008287 (1977-02-01), Verbrugge et al.
patent: 4450290 (1984-05-01), Sanderson et al.
Clive, D. L. J., et al., 1993. "Reaction of cis-Vicinal Dimethanesulfonates with Te.sup.2- . . . ", Journal of Chemical Society, Chemical Communications, No. 11, 7 Jun. 1993, Letchworth GB, pp. 923-924.
Clive, D. L. J., et al., 1980. "Alkali Metal O,O-Diethyl Phosphorotelluroates, a Reagent Class for Deoxygenation of Epoxides, Especially Terminal Epoxides", Journal of Organic Chemistry, vol. 45, No. 12, 6 Jun. 1980, Easton US, pp. 2347-2354.
Cosford, N. D. P., et al., 1991. "Selenium Nucleophiles for the Preparation of Antiviral Nucleosides", vol. 56, No. 6, 15 Mar. 1991, Easton US, pp. 2161-2165.
Prince, M., et al., 1966. "Sodium Selenide Vicinal Dihalide Elimination", vol. 31, No. 12, Dec. 1966, Easton US, pp. 4292-4293.
Clive, D. L. J., et al., 1982, "New Method for Coupling Allyl Halides: Use of Te.sup.2- Species", vol. 47, No. 9, 23 Apr. 1982, Easton US, pp. 1641-1647.
Johnson, R., et al., 1992. "Derivatives of 2',3'-Dithiouridine and (1-B-D-(2,3-Dithioxylofuranosyl))Uracil", vol. 33, No. 52, 22 Dec. 1992, Oxford GB, pp. 8151-8154.
Thiem, J., et al., 1985, "Synthesis and Perkow Reaction of Uridinen Derivatives", vol. 4, No. 4, 1985, pp. 487-506.
Tsujino, J., et al., 1989. "A Process for Preparation of 2'-Bromo-2',3'-Didehydro-2',3'-Dideoxycytidine as an Intermediate for 2',3'-Dideoxycytidine", vol. 111, No. 9, 28 Aug. 1989, Columbus, Ohio, US; abstract No. 78553n, p. 803, col. 1.
Haraguchi et al.(I), "Preparation and Reactions of 2'- and 3'-Vinyl Bromides of Uracil-Nucleosides: Versatile Synthons for Anti-HIV Agents", Tett. Lett., 32(28), 3391-3394 (1991).
Haraguchi et al.(II), "Nucleosidic Enol Esters: A Versatile Tool for the Synthesis of 3'-Carbon-Substituted Nucleosides", Tett. Lett., 32(6), 777-780 (1991).
Wrensford et al., "Synthesis of 3-Bromo-6-ethenyltetrahydro-2,2,6-trimethyl-2H-pyran", Tett. Lett., 31(10), 4257-4260 (1991).
T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd Ed., Wiley, 1991; Ch. 2, pp. 11-14; Ch. 3, pp. 143-144; Ch. 7, pp. 309-315.
"Tellurium", W. C. Cooper, Ed., Van Nostrand Reinhold, New York, 1971, pp. 188, 274-280.
M. Sekine et al., J. Org. Chem., 1990, 55, 924-928.
"Selenium", R. A. Zingaro et al., Eds, Van Nostrand Reinhold, New York, 1974, pp. 438-439, 530-545.
E. Block, Org. Reacts., 1984, 30, 457.
Chemical and Engineering News, 1991, Oct. 14, p. 17.
"Naming and Indexing of Chemical Substances for Chemical Abstracts, A Reprint of Appendix IV to 1982 Index Guide", A. Chem. Soc. para 203.
L. I. Fieser et al., Reagents for Organic Synthesis, vol. 1, Wiley, New York, 1967, pp. 662-664.
A. B. Harvey et al., J. Chem. Phys., 1969, 50, 4949-4961.
M. M. Mansuri et al., J. Org. Chem. 1989, 54, 4780-4785.
B. Kaskar et al., J. Heterocyclic Chem., 1989, 26, 1531-1533.
T. Yamaguchi et al., Nucleosides and Nucleotides, 1992, 11, 373-382.
P. Kumar et al., Nucleosides and Nucleotides, 1992, 11, 401.
G. Brauer, Ed. "Handbuck der Praparativen Anorganischem Chemie", Ferdinand Enke: Stuttgart, 1975; vol. I, p. 431.
J. B. Lambert et al., J. Org. Chem., 1979, 44, 1480-1485.
H. A. Shonle et al., J. Am. Chem. Soc., 1921, 43, 361-365.
M. Kawana et al., Bull. Chem. Soc. Jpn., 1981, 54, 1492-1504.
Taniguchi et al., Tetrahedron 1974, 30, 3574-3552.
K. Koga et al., Tetrahydron Lett. 1971, 263-266.
Codington et al., J. Org. Chem., 1964, 29, 558.
R. S. Tipson et al., Ed. "Synthesis Procedures in Nucleic Acid Chemistry", Wiley, 1968, vol. I, pp. 441-442.
J. J. Fox et al., J. Am. Chem. Soc., 1957, 79, 2775-2778.
N. D. P. Cosford et al., J. Org. Chem., 1991, 56, 2161-2165.
D. M. Brown et al., J. Chem. Soc., 1956, 2384-2387.
H. U. Blank et al., Justus Leibigs Ann. Chem., 1970, 742, 16-28.
H. P. M. Fromageot et al., Tetrahedron, 1967, 23, 2315-2331.
Y. Amino et al., Bull. Chem. Soc., 1991, 64, 620-623.
R. Vinayak et al., Nucleic Acids Research, 1992, 20, 1265-1269.
Aldrich Chemical Co., J. Org. Chem., Dec. 1990, 55, #25 (Back Cover).
P. Prince et al., J. Org. Chem., 1966, 31, 4292-4293.
L. Engman, Tetrahedron Lett., 1982, 23, 3601-3602.
T. K. Raja, Indian J. Chem., 1980, 19B, 812-813.
D. Clive et al., J. Org. Chem., 1980, 45, 2347-2354.
IUPAC Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F and H, 1979, Pergamon Press, Oxford.
D. Clive et al., J. Org. Chem., 1982, 47, 1641-1647.
M. Sekine et al., J. Org. Chem., 1990, 55, 924-928.

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