Intermediates in the synthesis of 1,3-oxathiolanyl cytosine nucl

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

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536 285, 536 2851, 536 2852, 549 63, C07D33336, C07D33342, C07H 1900

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056937873

ABSTRACT:
The present invention relates to highly diastereoselective processes for production of cis-nucleosides and nucleoside analogues and derivatives in high optical purity and intermediates useful in those processes.

REFERENCES:
patent: 4231945 (1980-11-01), McCombie
patent: 4383114 (1983-05-01), Vince
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
Goodman, "Chemical Syntheses and Transformations of Nucleosides," in Basic Principles in Nucleic Acid Chemistry, vol. 1, Academic Press, New York, 1974, pp. 106-110.
March, Advanced Organic Chemistry, McGraw-Hill Book Co., New York, 1968, pp. 896-897.
M. Fieser, Reagents for Organic Synthesis, vol. 8, Wiley-Interscience, New York, 1980, pp. 261-263.
M. Fieser, Reagents for Organic Synthesis, vol. 12, Wiley-Interscience, New York, 1986, pp. 543-547.
Chu et al., "Synthesis and Structure-Activity Relationships of 6-Substituted 2',3'-Dideoxypurine Nucleosides as Potential Anti-Human Immunodeficiency Virus Agents," J. Med. Chem., 33(6), 1553-1561 (1990).
Farina et al., "A New Synthesis of 2',3'-Dideoxynucleosides for AIDS Chemotherapy," Tett. Letters, 29(11), 1239-1242 (1988).
Mansuri et al., "Preparation of the Geometric Isomers of DDC, DDA, D4C and D4T as Potential Anti-HIV Agents," Bioorganic & Medicinal Chem. Letters, 1(1), 65-68 (1991).
Vince et al., "Synthesis and Anti-HIV Activity of Carbocyclic 2',3'-Didehydro-2',3'-dideoxy-2,6-Disubstituted Purine Nucleosides," J. Medicinal Chem., 33(1), 17-21 (1990).
Wilson et al., "The Synthesis and Anti-HIV Acivity of Pyrimidinyl Dioxolanyl Nucleosides", Bioorganic & Medicinal Chem. Letters, 3(2), 169-174 (1993).
J.W. Beach et al., "Synthesis of Enantiomerically Pure Antiviral Agent Against Hepatitis B Virus (HBV) and Human Immunodeficiency Virus (HIV)", J. Org. Chem., vol. 57, pp. 2217-2219 (1992).
B.R. Belleau, et al., "Oxidative Degradation of L-Ascorbic Acid Acetals to 2',3'-Dideoxy-3'-Oxaribofuranosides. Synthesis of Enantiomerically Pure 2',3'-Dideoxy-3'-Oxacytidine Stereoisomers as Potential Antiviral Agents", Tetrahedron Lett., vol. 33, pp. 6949-6952 (1992).
W-B. Choi, et al., "In Situ Complexation Directs the Stereochemistry of N-Glycoslylation in the Synthesis of Oxathiolanyl and Dioxolanyl Nucleoside Analogues", J. Am. Chem. Soc., vol. 113, pp. 9377-9379 (1991).
W-B. Choi, et al., "Synthesis, Anti-Human Immunodeficiency Virus, and Anti-Hepatitis B Virus Activity of Pyrimidine Oxathiolane Nucleosides", Bioorg. & Med. Chem. Lett., vol. 3(4), pp. 693-696 (1993).
C.K. Chu et al., "Enantiomeric Synthesis of (+)-BCH-189 D-Mannose and Its Anti-HIV Activity", J. Org. Chem., vol. 56, pp. 6503-6505 (1991).
P. Faury, et al., "Synthesis of Tetrazole Oxathiolane Nucleoside Analogues and Their Evaluation as HIV-1 Antiviral Agents", Nucleosides & Nucleotides, vol. 11(8), pp. 1481-1488 (1992).
G. Hesse et al., "Mercapto-acetaldehyd und Dioxy-1,4-dithian", Chem. Ber., vol. 85, pp. 924-932 (1952).
D.C. Humber et al., "Expeditious Preparation of (-)-2'-Deoxy-3'-Thiacytidine (3TC)", Tetrahedron Lett., vol. 33, pp. 4625-4628 (1992).
L.S. Jeong, et al., "An Efficient Synthesis of Enantiomerically Pure (1992).
L.S. Jeong, et al., "Asymmetric Synthesis and Biological Evaluation of .beta.-L-(2R, 5S)-and .alpha.-L-(2R, 5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HiV Agents", J. Med. Chem., vol. 36, pp. 181-195 (1993).
L.S. Jeong, et al., "Structure-Activity Relationships of .beta.-D-(2S,5R)-and .alpha.-D-(2S,5S)-1,3-Oxathiolanyl Nucleosides as Potential Anti-HIV Agents", J. Med. Chem., vol. 36, pp. 2627-2638 (1993).
H. Jin, et al., "Unexpected Effects of Lewis Acids in the Synthesis of Optically Pure 2'-Deoxy-3'-Oxayctidine Nucleoside Analogues", Tetrahedron: Asymmetry, vol. 4(2), pp. 211-214 (1993).
J.L. Kraus, et al., "Synthesis of New 2,5-Disubstituted 1,3-Oxathiolanes. Intermediates in Nucleoside Chemistry", Synthesis, pp. 1046-1048 (1991).
J.M. McIntosh et al., "2-Mercaptoaldehyde Dimers and 2,5-Dihydrothiphenes From 1,3-Oxathiolan-5-ones", Can. J. Chem., vol. 61, pp. 1872-1875 (1983).
R. Storer et al., "The Resolution And Absolute Stereochemistry of the (BCH-189): Equipotent Anti-HIV Agents", Nucleosides & Nucleotides, vol. 12, pp. 225-236 (1993).
E. Vedejs, et al., "Method for Sulfide S-Benzylation or S-Allylation Using Trimethylsilyl Triflate Activated Benzyl or Allyl Ethers", J. Org. Chem., vol. 46, pp. 3353-3354 (1981).

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