2',3'-dideoxy-4'-thioribonucleosides and synthetic precursors th

Details 2',3'-dideoxy-4'-thioribonucleosides and synthetic precursors th 2',3'-dideoxy-4'-thioribonucleosides and synthetic precursors th

1993-10-29

1995-12-26

Robinson, Douglas W.

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

Organic compounds

Carbohydrates or derivatives

536 2714, 536 282, 544264, 544304, 549 13, 549 28, C07G 300, C07H 1900, C07D33500

Patent

active

054789281

ABSTRACT:
2',3'-dideoxy-4'-thioribonucleosides useful as antiviral agents in the treatment and prevention of AIDS are disclosed. In accordance with one aspect of the invention there are provided compounds of the formula ##STR1## where X.dbd.H, N.sub.3 or F, and B is a member selected from the group consisting of pyrimidine, 5-azapyrimidine, 6-azapyrimidine, 3-deazapyrimidine, purine, 3-deazapurine, 7-deazapurine, 8-azapurine, and 2-azapurine bases. The intermediate 1-O-acetyl-5-O-t-butyldiphenylsilyl-4-thio-2,3-dideoxyribofuranose is useful in the production of certain of the 2',3'-dideoxy-4'-thioribonucleosides. Other intermediates include the 4-thio-2,3-dideoxyribofuranose having different hydroxyl protecting groups and leaving groups.

REFERENCES:
patent: 5128458 (1992-07-01), Montgomery et al.
Hanessian et al., "Stereochemical Control of Nature's Biosynthetic Pathways: A General Strategy for the Synthesis of Polypropionate-Derived Structural Units for a Single Chiral Progenitor," Tetrahedron, 43(21), 5505-5572 (1987).
R. S. Root-Bernstein (I), "AIDS Is More Than HIV: Part I", Genetic Engineering News, Sep. 1, 1992, pp. 4-6.
R. S. Root-Bernstein (I), "AIDS Is More Than HIV: Part II", Genetic Engineering News, Sep. 15, 1992, pp. 4-5.
Dyson et al.(I), "The Synthesis and Antiviral Activity of Some 4'-Thio-2'-deoxynucleoside Analogs," Nucleic Acids Res. Symps. Ser., (24), 1-4 (1991); Chem. Abstr., 117(21), p. 31, Abstr. No. 204617a, (1992) only Abstract supplied.
Dyson et al. (II), "The Synthesis and Antiviral Properties of .EPSILON.-5-(2-bromovinyl)-4'-thio-2'-deoxyuridine," J. Chem. Soc., Chem. Comm., (11), 741-742 (1991).
Dyson et al. (III), "The Synthesis and Antiviral Activity of Some 4'-Thio-2'-deoxy Nucleoside Analogues," J. Med. Chem., 34, 2782-27-86 (1991).
Secrist et al., "Synthesis and Anti-HIV Activity of 4'-Thio-2',3'-dideoxynucleosides," J. Med. Chem., 35, 533-538 (1992).
Adley et al., "Thio-Sugars. Part I. The Thiofuranose Ring," J. Chem. Soc., 1966(Sec. C), 1287-1290.
Owen et al., "Thio-Sugars. Part II. The Thiofuranose Ring," J. Chem. Soc., 1966(Sec. C), 1291-1296.
Clayton et al., "Derivatives of D-Ribothiafuranose," Chem. & Ind., 1962, 1795-1796.
Miura et al., "4'-Thioadenosine as a Novel Inhibitor of S-Adenosylhomocysteine Hydrolase and an Inducer for the Differentiation of HL-60 Human Leukemia Cells," in Purine and Pyimidine Metabolism V, Part B, Nyhan et al. eds., Plenum Publ Co., 1986, p. 667+?.
Ritchie et al., "Addition of Pseudohalogens to Unsaturated Carbohydrates. VI Synthesis of 4'-Thiacordycepin," Can. J. Chem., 56, 794-802 (1978).
Reist et al., "Thio Sugars. Synthesis of the Adenine Nucleosides of 4-Thio-D-xylose and 4-Thio-D-arabinose," J. Org. Chem., 33(1), 189-192 (1968).
Ototani et al., "Preparation and Antitumor Activity of 4'-Thio Analogs of 2,2'-Anhydro-1-.beta.-arabinofuranosylcytosine," J. Med. Chem., 17(5), 535-537 (1974).
Fu et al., "An Alternative Synthesis of Anomeric Methyl 2-Deoxy-4-thia-D-erythro-pentofuranosides," J. Org. Chem., 41(24), 3831-3834 (1976).
Whistler et al., "Anomeric Methyl 4-Thio-D-arabinosylfuranosides," J. Org. Chem., 35(2), 519-521 (1970).

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