Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-06-05
1998-04-28
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 285, 536 2852, 536 41, 536 276, 536 278, 536 2781, 536 2853, 536 2722, 536 271, 536 281, 536 184, 536 187, 549 63, C07H 1900
Patent
active
057445966
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: 4882316 (1989-11-01), Lambert et al.
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
Lukevics et al., Nucleosides Synthesis--Organosilicon Methods, Ellis Norwood, New York, NY, 1991, only "Table of Contents" and Heterocyclic Base Index (pp. 445-452) supplied.
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 Syntheisis, 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.
M.N. Romanelli et al., "Enantioselectivity of Muscarinic Antagonists. Related 3-oxides", Journal of Medicinal Chemistry, vol. 31, pp. 1698-1702 (1988).
Aggarwal et al. "Synthesis and Biological Evaluation of Prodrugs of Zidovudine", J. Med. Chem., vol. 33, pp. 1505-1510 (1990).
Beres et al., "Stereospecific Synthesis And Antiviral Properties of Different Enantiomerically Pure Carbocylic 2'-Deoxyribonucleoside Analogues Derived From Common Chiral Pools: Chem., vol. 33, pp. 1353-1360 (1990).
Chu et al., "An Efficient Total Synthesis of 3'-Azido-3'-Deoxythymidine (AZT) and 3'-Azido-2', 3'-dideoxyuridine (AZDDU. CS-87) From D-Mannitol", Tetrahedon lett., vol. 29 (42), pp. 5349-5352 (1988).
Chu et al., "General Synthesis of 2',3'-Dideoxynucleosides And 2',3'-Dideoxynuleosides", J. Org. Chem., vol. 54, pp. 2217-2225 (1989).
Choi, et al., "In Situ Complexation Directs the Stereochemistry of N-Glycosylation in the Synthesis of Oxathiolanyl and Dioxolanyl Nucleoside Analogues", J.Am. Chem. Soc., vol. 113, pp. 9377-9379 (1991).
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., vol. 33, pp. 1553-1561 (1990).
Chu et al., "A Highly Stereoselective Glycosylation of 2-(Phenylselenenyl)-2,3-Dideoxyribose Derivative With Thymine: Synthesis of 3'-Deoxy-2',3'-Didehydrothymidine And 3'-Deoxythymidine", J. Org. Chem., vol. 55, pp. 1418-1420 (1990).
Chu et al., "Asymmetric Synthesis Of Enantiomerically Pure (-)-(1'R,4'R)-Dioxolane-Thymine And Its Anti-HIV Activity", Tetrahedron Lett., vol. 32(31), pp. 3791-3794 (1991).
Evans et al. "Divergent Asymmetric Syntheses of Dioxolane Nucleoside Analogues", Tetrahedron:Asymmetry, vol. 4(11), pp. 2319-2322 (1993).
Farina and Benigni, "A New Synthesis Of 2',3'-Dideoxynucleosides For AIDS Chemotherapy", Tetrahedron Lett., vol. 29(11), pp. 1239-1242 (1988).
Gosselin et al., "Systematic Synthesis And Biological Evaluation of .alpha.- and .beta.-D-Lyxofuranosyl Nucelosides Of The Five Naturally Occurring Nucleic Acid Bases", J. Med. Chem., vol. 30, pp. 982-991 (1987).
Herdewijn et al., "3'-Substituted 2',3'-Dideoxynucleoside Analogues as Potential Anti-HIV (HLTV-III/LAV) Agents", J. Med. Chem., vol. 30, pp. 1270-1278 (1987).
Huryn et al., "Synthesis Of Iso-ddA, Member Of A Novel Class Of Anti-HIV Agents", Tetrahedron Lett., vol. 30(46), pp. 6259-6262 (1989).
Huryn et al., "Synthesis of Iso-ddA, Member Of A Novel Class Of Anti-HIV Agents-Dioxolane-T. A New 2'''-Dideoxynucleoside Prototype With In Vitro Activity Against HIV", Chemtracts-Organic Chemistry, vol. 3, pp. 249-251 (1990).
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(2), pp. 181-195 (1993).
Kim, et al., "1,3-Dioxolanyl Purine Nucleosides (2R,4R) and (2R,4S) with Selective Anti-HIV-1 Activity in Human Lymphocytes", J. Med. Chem., vol. 36, pp. 30-37 (1993).
Kraus et al., "Synthesis of New 2,5-Substituted 1,3-Oxathiolanes. Intermediates in Nucleoside Chemistry", Synthesis, pp. 1046-1048 (1991).
Lin et al., "Synthesis and Antiviral Activity of Various 3'-Azido, 3'-Amino, 2', 3'-unsaturated, and 2', 3'-Dideoxy Analogues of Pyrimidine Deoxyribonucleosides Against Retroviruses", J. Med. Chem., vol. 30, pp. 440-444 (1987).
Mansuri et al., "Preparation of the Geometric Isomers of DDC, DDA, D4C and D4T As Potential Anti-HIV Agents", Biorg. & Med. Chem. Lett., vol. 1(1), pp. 65-68 (1991).
Norbeck et al., "(+)-Dioxolane-T", Tetrahedron Lett., vol. 30, pp. 6263-6266 (1989).
Okabe et al., "Synthesis of the Dideoxynucleosides ddC And CNT From Glutamic Acid, Ribonolactone, and Pyrimidine Bases", J. Org. Chem., vol. 53, pp. 4780-4786 (1988). pyrimidine 2', 3'-Dideoxyribonucleosides", Liebigs Ann. Chem., pp. 227-232 (1990).
Siddiqui et al., "Antiviral Optically Pure Dioxolane Purine Nucleosides Analogues", Bioorg. & Med. Chem. Lett., vol. 3(8), pp. 1543-1546 (1993).
Ueda and Watanabe, "Synthesis and Optical Properties of 2,3-Dideoxy-D-Erythro -Hex-2-Enopyranosyl Nucleosides (Nucleosides And Nucleotides. LXII)", Chem. Pharm. Bull., vol. 33(9), pp. 3689-3695 (1985).
Vedejs et al., "Method for Sulfide S-Benzylatian or S-Allylation Using Trimethylsilyl Triflate Activated Benzyl or Ally Ethers", J. Org. Chem., vol. 46, pp. 3353-3354 (1981).
Vince and Hua,"Synthesis and Anti-HIV Activity of Carbocylic 2',3'-Didehydro-2',3'-Dideoxy 2,6-Disubstituted Purine Nucleosides", J. Med. Chem., vol. 33, pp. 17-21 (1990).
Wilson and Liotta, "A General method For Controlling Glycosylation Stereochemistry In The Synthesis Of 2'-Deoxyribose Nucleosides", Tetrahedron Lett., vol. 31(13), pp. 1815-1818 (1990).
Wilson et al., "The Synthesis and Anti-HIV Activity of Pyrimidini Dioxolanyl Nucleosides", Bioorg. Med. Chem. Lett., vol. 3(2), pp. 169-174 (1993).
Mansour Tarek
Tse Allan H. L.
Biochem Pharma Inc.
Crane L. Eric
Haley, Jr. James F.
Kight John
McDonell Leslie A.
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