Process for preparing dithiophosphate oligonucleotide analogs vi

Details Process for preparing dithiophosphate oligonucleotide analogs vi Process for preparing dithiophosphate oligonucleotide analogs vi

1989-11-02

1993-06-08

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 2531, C07H 1910, C07H 1920

Patent

active

052180883

ABSTRACT:
A method for synthesis of oligonucleotide analogs having dithiophosphate internucleosidic linkages is described. Monohalohydrocarbylthiophosphoramidites are utilized to prepare nucleoside thiophosphoramidite intermediates which are activated for nucleoside coupling with tetrazole catalysts. Sulfur oxidation and dehydrocarbylation of the coupled thiophosphite intermediates provide oligonucleotide analogs having achiral dithiophosphate internucleosidic linkages.

REFERENCES:
patent: 4668777 (1987-05-01), Caruthers et al.
"Deoxynucleoside Phosphoramidites--A New Class Of Key Intermediates For Deoxypolynucleotide Synthesis", Tetrahedron Letters, vol. 22, No. 20, pp. 1859-1862, 1981, Beaucage et al.
"An Investigation Of Several Deoxynucleoside Phosphoramidites Useful For Synthesizing Deoxyolignucleotides", McBride et al., Tetrahedron Letters, vol. 24, No. 3, pp. 245-248, 1983.
"Synthesis Of Dinucleoside Phosphorodithioates Via Thioamidites", Brill, et al., Tetrahedron Letters, vol. 29, No. 43 pp. 5517-5520, 1988.
"Synthesis Of Oligodeoxynucletides Containing Specific Methylphosphonothioate and Dithioate Moieties", Brill, et al., Aug. 8-12, 1988.
"Preparation Of A Deoxynucleside Thiophosphoramidite Intermediate In The Synthesis Of Nucleoside Phosphorodithioates", Faraschtschi & Gorenstein, Tetrahedron Letters, vol. 29, No. 52, pp. 6843-6846, 1988.
"Synthesis Of Oligodeoxynucleoside Phosphorodithioates Via Thioamidites", Brill, et al., J. Amer. Chem. Soc., 1989, vol. 111, pp. 2321-2322.
Chemical Abstracts No. 107:198467b, Al'fonsov et al. Zh. Obshch. Khim, 56(8), 1697-1699 (1986).
Chemical Abstracts No. 96:85bb8d, Sinyashin et al. Zh. Obshch. Khim. 51(11), 2410-2413, (1981).

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