N-protected-2'-O-methyl-ribonucleosides and N-protected 2'-O-met

Details N-protected-2'-O-methyl-ribonucleosides and N-protected 2'-O-met N-protected-2'-O-methyl-ribonucleosides and N-protected 2'-O-met

1991-08-30

1993-05-25

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 2781, 536 2671, 536 268, 536 285, C07H 19167

Patent

active

052141357

ABSTRACT:
This invention is directed to N (amino)-protected-2'-O-methyl (methoxy)-5'-dimethoxytrityl (dimethoxytrityl) ribonucleosides (Group I compounds) and to N-protected-2'-O-methyl-5'-dimethoxytrityl-3'-ribonucleoside cyanoethyl N,N-diisopropyl phosphoramidites (Group II compounds). This invention is further directed to the processes involved in producing these compounds. The purification processes produce products in Group I with purity in excess of 99.50% and up to 99.8%. The purity of the products in Group II ranges in excess of 99.8% and up to 99.9%.

REFERENCES:
patent: 4500707 (1985-02-01), Caruthers et al.
Gaffney et al., "Synthesis and Characterization of a Set of Four Dodecadeoxyribonucleoside Undecaphosphates Containing O.sup.6 -Methylguanine opposite Adenine, Cytosine, Guanine, and Thymine", Biochemistry, 23, 5696-5691 (1984).
Borowy-Borowski et al., "Study of Side Reactions Occurring during Synthesis of Oligodeoxynucleotides Containing O.sup.6 -Alkyldeoxyguanosine Residues at Preselected Sites," Biochemistry, 26, 2465 (1987).
Kyellberg et al., "Studies on the Alkylation of Derivatives of Guanine," Nucleosides & Nucleotides, 8(2), 225-256 (1989).
Ishido et al., Chem. Abstr., 109:234171q (1988); abstract of PCT Intl. Application WO 88 03,149.
Gladkaya et al., Chem. Abstr., 112:198,947m (1990); Abstract only.
Kochetkov et al., Organic Chemistry of Nucleic Acids, Part B, Plenum Press, New York, 1972, see pp. 458-460.
Takaku et al., Chem. Lett., 1986, 1005-1008.
Rozners et al., Bioorg. Khim., 16(11), 1531-1536 (1990).
Fujii et al., Chem. Pharm. Bull., 35(7), 3066-3069 (1987).
Kamimura et al., Nucleic Acids Research Symposim Series, No. 12, IRL Press Ltd., Oxford England, 1983, pp. 63-65.

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