5'-O-Dans EOC modified nucleosides and methods for preparing sam

Details 5'-O-Dans EOC modified nucleosides and methods for preparing sam 5'-O-Dans EOC modified nucleosides and methods for preparing sam

1995-05-09

1997-05-20

Wilson, James O.

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

Organic compounds

Carbohydrates or derivatives

536 2721, 536 2761, 536 2762, 536 2763, 536 278, 536 2781, 536 2854, C07H 100

Patent

active

056313624

ABSTRACT:
Dansylethoxycarbonyl (Dans-EOC) groups which can be employed as base-labile 5'hydroxyl protective groups in chemical oligonucleotide synthesis are disclosed. These groups allow the preparation of a compound of the formula (I) ##STR1## which comprises reacting the compound of the formula (II) ##STR2## with a chlorocarbonyl donor.

REFERENCES:
patent: 3781310 (1973-12-01), Meininger et al.
patent: 4997928 (1991-03-01), Hobbs, Jr.
Lehmann et al., Nucleic Acid Research, vol. 17, No. 7, pp. 2379-2390 (1989).
S.L. Beaucage et al., "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach," Tetrahedron, 48 (12) (1992) pp. 2223-2311.
R. Charubala et al., Tetrahedron Letters, vol. 21, pp. 1933-1936 (1980).
Hawley's Condensed Chemical Dictionary, 11th Edition, 1987, p. 839.
E. Winnacker, "From Genes to Clones," 1987, Chapter 2.3.
E. Sonveaux, "The Organic Chemistry Underlying DNA Synthesis", Bioorganic Chemistry, 14, 274-325, 1986.
C. Lehmann et al., "Solid-phase synthesis of oligoribonucleotides using 9-fluorenylmethoxycarbonyl (Fmoc) for 5'-hydroxyl protection", Nucleic Acid Research, vol. 17, No. 7, 2379-2390, Apr. 1989.

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