Method and cyclic carbonates for nucleotide analogues

Details Method and cyclic carbonates for nucleotide analogues Method and cyclic carbonates for nucleotide analogues

1995-12-27

1997-11-11

Shah, Mukund J.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544243, 544244, 544264, 544265, 544267, 544276, 544277, 544309, 544311, 544312, 544314, 544316, 544317, C07D31728, C07D47334, C07D31736, C07D47316

Patent

active

056866291

ABSTRACT:
An improved method for the preparation of acyclic nucleotide analogues comprises first condensing a cyclic carbonate with a purine or pyrimidine base and then reacting the alkylated base with an activated phosphonate. Novel cyclic carbonates are employed to yield the desired phosphonylmethoxyalkyl nucleotide analogues.

REFERENCES:
patent: 3558656 (1971-01-01), Pfeiffer et al.
patent: 4281125 (1981-07-01), DePompei et al.
patent: 4322533 (1982-03-01), Lesher et al.
patent: 4563473 (1986-01-01), Hofman et al.
patent: 4724233 (1988-02-01), De Clercq et al.
patent: 4808716 (1989-02-01), Holy et al.
patent: 5142051 (1992-08-01), Holy et al.
Katzhandler, J. et al. J. Chem. Soc. Perkin Trans. II, pp. 1729-1739 (1989).
Greene, T.W. et al. Protective Groups in Organic Synthesis, pp. 362-368 (1991).
Ichinose, E. et al. Chemical Abstracts 115:94511 (1991).
Grahe, G. et al. Chemical Abstracts 111:134 129 (1989).
Kawabata, O. et al. Chemical Abstracts 109:219655 (1988).
Bronson et al., "Synthesis and Antiviral Activity of Phosphonylmethoxyethyl Derivatives of Purine and Pyrimidine Bases," Nucleotide Analogues 72-87 (1989).
Dodd et al, "Preparation of Glycerols protected at the 2-hydroxy-group and their application to the Synthesis of Lipids," J Am Chem Soc 1(21):2273-2277 (1976).
Foglia et al, "Oxidation of 1-O-(Alk-1-enyl)-2,3Di-O-Acylglycerols: Models for Plasmalogen Oxidation," Lipids 23(5):430-444 (1988).
Gigg et al, "Preparation of Unsymmetrical Diglycerides," J Am Chem Soc 6: 431-434 (1967).
Gomez et al, "Syntheses of D-Glyceraldehyde 2,3-Carbonate, D-Glyceraldehyde 2,3-Diacetate, and Racemic and sn Glyceral 1,2-carbonate," AN QUIM 80(1): 42-44 (1984).
Hirth et al, "Synthesis of Glycery Lether Phosphatides. Part 2. Preparation (Oleyl-PAF)," HEV CHIM ACTA 66(4):1210-1240 (1983).
Holy et al., "Synthesis of 9-(2-Phosphonylmethoxyethyl)Adenine and Related Compounds," Collect Czech Chem Commun 52:2801-2809 (1987).
Holy et al., "Synthesis of N-(2,3-Dihydroxypropyl) Derivatives of Heterocyclic Bases," Collect Czech Chem Commun 43(8):2054-2061 (1978).
Holy, A., "Synthesis of New Mono-and Disubstituted Hydroxyalkyl and Aminoalkyl Derivatives of Heterocyclic Bases," Collect Czech Chem Commun 43:3444-3465 (1978).
Holy, A., "Synthesis of Racemic and Optically Active erythro-and threo-9(2,3,4-Trihydroxybutyl)Adenines and Related Compounds," Collect Czech Chem Commun 593-612 (1979).
Holy, A., "Synthesis of Some 2,3-Dihydroxypropyl Derivatives of Purine Bases," Collect Czech Chem Commun 3103-3117 (1978).
Juaristi et al., "Use of Hexamethyl Phosphoramide (HMPA) in the Alkylation of Aromatic Amines: Synthesis of Azetidines, Pyrrolidines, Piperidines and Hexahydroazepines,"Tet Lett 45(3):629-636 (1989).
Katzhendler et al, "Conformational Studies of Substituted Five-membered Cyclic Carbonates and Related Compounds by MNDO, and the X-Ray Crystal structure of 4-chlorophenyloxymethyl)-1,3-dioxolan-2-one," J Chem Soc Perkin Trans II 2(11):1729-1739 (1989). and 9-Substituted Purines as Potential Antiparasitic Agents," J Het Chem 20:295-299 (1983).
Oehlenschlaeger et al., "Synthesis and Mass Spectrometry of 1-Acyl and 3-Acyl -sn-Glyercol Carbonates," Lipids 13(8):557-562 (1978).
Ramaiah, M., "A New Convenient Method for Esterification Using the Ph3P/CC14 System," J Org Chem 50(24):4991-4993 (1985).
Takeuchi et al., "Triazolopyridazin-3-one derivatives," Chem AB 106:5066 (1984).
Tam, W., "Carbonylation of Beta-Aminoethanols, Diols, and Diol Amines," J Org Chem 51(15):2977-1981 (1986).
Ueda, N. et al., "Vinyl Compounds of Nucleic Acid Bases. I. Synthesis of N-Vinyluracil, N-Vinylthymine, and N-Vinyladenine," Die Makromolekulare Chemie 120:13-20 (1968).
Zhelvakova et al, "Lipids. Synthesis of 1,2-Diacyl-sn-Glycerols from D-mannitol Using a Carbonate Protection," Zh Org Khim 6(10):1987-1992 (1970).

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