C.sup.ac -methylphosphonamidites and methods for preparing methy

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 268, C07H 102, C07H 1920

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057314292

ABSTRACT:
A compound of general formula ##STR1## wherein R is methyl R' is selected from the group consisting of trityl and pixyl, and R" is H or OMe. These compounds may advantageously be employed in the synthesis of oligonucleotides by conventional methods, such as automated solid phase synthesis. Use of ethylene diamine in the cleavage and deprotection procedure substantially eliminates the formation of undesirable side products.

REFERENCES:
patent: 5348868 (1994-09-01), Reddy et al.
patent: 5428148 (1995-06-01), Reddy et al.
Miller, Paul S.; "Oligonucleoside Methylphosphonates as Antisense Reagents", Biotechnology, vol. 9, Apr. 1991, pp. 358-362.
Miller, Paul S., et al; "Solid-Phase Syntheses of Oligodeoxyribonucleoside Methylphosphonates"; Biochemistry 1986, vol. 25, pp. 5092-5097.
Miller, Paul S. et al; "Preparation of Oligodeoxyribonucleoside Methylphosphonates on a Polystyrene Support"; Nucleic Acids Research, vol. 11, No. 18, 1983.
Hogrefe, Richard I, et al; "Deprotection of Methylphosphonate Oligonucleotides Using a Novel One-Pot Procedure"; Nucleic Acids Research, 1993, vol. 21, No. 9, pp. 2031-2038.
Agrawal, Sudhir, et al; "Oligodeoxynucleoside Methylophosphonates: Synthesis and Enzymic Degradation"; Tetrahedron Letters, vol. 28, No. 31, pp. 3539-3542, 1987.
Kandimalla, Ekambar R.; et al; "Synthesis and Properties of 2'-O-Methylribonucleotide Methylphosphonate Containing Chimeric Oligonucleotides"; Nucleosides & Nucleotides, 14(3-5), pp. 1031-1035 (1995).
Vaghefi, Morteza M., et al; "A Convenient High Yield Synthesis of N4-Isobutyryl-2'-o-Methylcytidine and Its Monomer Units for Incorporation into Oligonucleotides", Nucleosides & Nucleotides, 12(10), pp. 1007-1013 (1993).

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