Process for the preparation of 2'-deoxyribofuranosyl nucleosides

Details Process for the preparation of 2'-deoxyribofuranosyl nucleosides Process for the preparation of 2'-deoxyribofuranosyl nucleosides

1978-05-10

1980-01-08

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

424180, C07H 1700

Patent

active

041828593

ABSTRACT:
2'-Deoxyribofuranosyl nucleosides having the formula: ##STR1## , wherein R.sup.1 is a hydrogen atom, a straight-chain or branched alkyl group of 1-6 carbon atoms, a phenyl or benzyl group, a methoxy group, a halogen atom, a nitro group, a nitrile group or an amino group which can be mono- or disubstituted by alkyl of 1-6 carbon atoms, or in which the nitrogen atom thereof is part of a 5- or 6-membered ring, or a perfluoroalkyl group of 1-6 carbon atoms; R.sup.2 is a hydrogen atom or a halogen atom; and R.sup.3 and R.sup.4 are benzoyl, tolyl, p-chlorobenzoyl or p-nitrobenzoyl, which comprises reacting a 1-halogen derivative of a blocked 2-deoxy-D-ribose with a silylated pyrimidine derivative in an alkyl nitrile solvent in the presence of a mercury (II) salt at a temperature of about -10.degree. to about 40.degree. C. The biologically active .beta.-anomers can be separated from the resulting reaction mixture readily and in high yield. The disclosed process is particularly suitable as a means for producing the known antiviral compound .beta.-5-ethyl-2'-deoxyuridine.

REFERENCES:
patent: 3352849 (1967-11-01), Shen et al.
patent: 3354160 (1967-11-01), Duschinsky
patent: 3531464 (1970-09-01), Ryan et al.
patent: 3708469 (1973-01-01), Vorbruggen et al.
patent: 3748320 (1973-07-01), Vorbruggen et al.
patent: 3817980 (1974-06-01), Vorbruggen et al.
patent: 4082911 (1978-04-01), Vorbruggen
Kulikowski, T. and Shugar, D., J. Med. Chem., 1974, vol. 17, 269-273.

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