Chemical synthesis of methoxy nucleosides

Details Chemical synthesis of methoxy nucleosides Chemical synthesis of methoxy nucleosides

2005-12-06

2005-12-06

Wilson, James O. (Department: 1623)

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

Organic compounds

Carbohydrates or derivatives

C536S027600, C536S027810, C536S028500, C536S055300

Reexamination Certificate

active

06972330

ABSTRACT:
Process for chemical synthesis of methoxy nucleosides.

REFERENCES:
Azuma and Isono, “Transnucleosidation: An Improved Method for Transglycosylation from Pyrimidines to Purines,”Chem. Pharm. Bull.25(12):3347-3353 (1977).
Beigelman et al., “Alternate Approaches to the Synthesis of 2′-O-Me Nucleosides,”Nucleosides&Nucleotides14(3-5):421-425 (1995).
Broom and Robins, “Primary Processes in the Photochemistry of Tetramethyl-1,3-cyclobutanedione,”I Am. Chem. Soc.87(5):1144-1146 (1965).
Chanteloup and Thuong, “Efficient Synthesis of 2-O-Alkyl Ribonucleosides Using Trichloroacetimidate D-Ribofuranosides as Ribosyl Donors,”Tetrahderon Letters35(6):877-880 (1994).
Chavis et al., “Synthesis of 2′, 3′-Differentiated Ribonucleosides via Glycosylation Reactions with 2-O-Me or 2-O-TBDMS Ribofuranose Derivatives. 1. Pyrimidine Series,”J. Org. Chem.47:202-206 (1982).
Cotten et al., “2-O-Methyl, 2′-O-ethyl oligoribonucleotides and phosphorothioate oligodeoxyribonucleotides as inhibitors of the in vitro U7 snRNP-dependent mRNA processing event,”Nucleic Acids Research19:2629-2635 (1991).
Davoll et al., “A New Synthesis of Purine Nucleosides. The Synthesis of Adenosine, Guanosine and 2,6-Diamino-9-β-D-Ribofuranosylpurine,”J. Am. Chem. Soc.73:1650-1655 (1951).
Duval-Valentin, “Specific inhibition of transcription by triple helix-forming oligonucleotides,”Proc. Natl. Acad. Sci. USA89:504-508 (1992).
Egholm et al., “PNA hybridizes to complementary oligonucleotides obeying the Watson-Crick hydrogen-bonding rules,”Nature365:566-568 (1993).
Haga et al., “3-O-Methyl-D-allose and a facile route to 2- and 3-O-methyl-D-riboses,”Carbohydrate Research21:440-446 (1972).
Imazawa and Eckstein, “Facile Synthesis of 2′-Amino-2′-deoxyribofuranosyl Purines,”J. Org. Chem.44:2039-2041 (1979).
Inoue, Japanese Patent No. 61-291595, Dec. 22, 1986.
Inoue et al., “Synthesis and hybridization studies on two complementary nona(2′-O-methyl) ribonucleotides,”Nucleic Acids Research15:6131-6149 (1987).
Khwaja and Robins, “Purine Nucleosides. XVI. Synthesis of the Naturally Occurring 2′-O-Methylpurine Ribonucleosides and Related Derivatives,”Journal of the American Chemical Society88(15):3640-3643 (1966).
Leonard et al., “A Convenient Preparation of Protected 2′-O-Methylguanosine,”Nucleosides&Nucleotides11(6):1201-1204 (1992).
Limbach et al., “Summary: the modified nucleosides of RNA,” Nucleic Acids Research 22(12):2183-2196 (1994).
Martin et al., “The Action of Diazomethane on Ribonucleosides. Preparation of Ribonucleoside 2′- and 3′-Methyl Ethers,”Biochemistry7:1406-1412 (1968).
Nair and Richardson, “Modification of Nucleic Acid Bases via Radical Intermediates: Synthesis of Dihalogenated Purine Nucleosides,”Synthesis8:670-672 (1982).
Parmentier et al., “A Convergent Synthesis of 2′-O-Methyl Uridine,”Tetrahedron50:5361-5368 (1994).
Philips and Horwitz, “Nucleosides. XVII. Benzylation-Debenzylation Studies on Nucleosides,”J. Org. Chem.40(12):1856-1858 (1975).
Robins et al., “Nucleic Acid Related Compounds. 12. The Facile and High Yield Stannous Chloride Catalyzed Monomethylation of the Cis-Glycol System of Nucleoside by Diazomethane,”J. Org. Chem.13:1891-1899 (1974).
Robins et al., “Nucleic acid related compounds. 36. Synthesis of the 2′-O-methyl and 3′-O-methyl ethers of guanosine and 2-aminoadenosine and correlation of O-methylnucleoside13C nmr spectral shifts,”Canadian Journal of Chemistry59:3360-3364 (1981).
Ross et al., “General Preparative Synthesis of 2′-O-Methylpyrimidine Ribonucleosides,”J. Heterocyclic Chem.31:765-769 (1994).
Scaringe et al., “Chemical synthesis of biologically active oligoribonucleotides using β-cyanoethyl protected ribonucleoside phosphoramidites,” Nucl Acids Res. 18:5433-5441 (1990).
Sproat and Gait, “Ch. 4—Solid-phase Synthesis of Oligodeoxyribonucleotides by the Phosphotriester Method,” inOligonucleotide Synthesis: A Practical Approach,edited by Gait, IRL Press, Oxford, UK, pp. 83-115 (1984).
Sproat et al., “New synthetic routes to protected purine 2′-O'methylriboside-3′-O-phosphoramidites using a novel alkylation procedure,”Nucleic Acids Research18:41-49 (1990).
Srivastava et al., U.S. Patent No. 5,214,135, issued May 25, 1993, “N-Protected-2′-O-Methyl-Ribonucleosides and N-Protected 2′-O-Methyl-3′-Cyanoethyl-N,-N-Diisopropyl Phosphoramidite Ribonucleosides”.
Stein and Cheng, “Antisense Oligonucleotides as Therapeutic Agents—Is the Bullet Really Magical?”Science261:1004-1288 (1993).
Torrence et al., “Targeting RNA for degradation with a (2′-5′) oligoadenylate-antisense chimera,”Proc. Natl. Acad. Sci USA90:1300-1304 (1993).
Ueda, “Ch. 1—Synthesis and Reaction of Pyrimidine Nucleosides,”Chemistry of Nucleosides and Nucleotidesvol. 1, pp. 1-112, Townsend editor, Plenum Press, New York, New York (1988).
Usman et al., “Automated Chemical Synthesis of Long Oligoribonucleotides Using 2′-O-Silylated Ribonucleoside 3′-O-Phosphoramidites on a Controlled-Pore Glass Support: Synthesis of a 43-Nucleotide Sequence Similar to the 3′-Half Molecule of anEscherichia coliFormylmethoionine tRNA,”J. Am. Chem. Soc.109:7845-7854 (1987).
Verheyden et al., “Synthesis of Some Pyrimidine 2′-Amino-2′-deoxynucleosides,”J. Org. Chem.36:250-254 (1971).
Wincott et al., “Synthesis, deprotection, analysis and purification of RNA and ribozymes,” Nucleic Acids Research 23(14):2677-2684 (1995).
Yamauchi et al., “Methylation of Nucleosides with Trimethylsulfonium Hydroxide. Effects of Transition Metal Ions,”J. Org. Chem.45:3865-3868 (1980).

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