Process for preparing 2'-deoxy-5-trifluoromethyl-beta-uridine

Details Process for preparing 2'-deoxy-5-trifluoromethyl-beta-uridine Process for preparing 2'-deoxy-5-trifluoromethyl-beta-uridine

1990-02-20

1991-04-09

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

C07H 100

Patent

active

050066463

ABSTRACT:
The present invention is a process for preparing 2'-deoxy-5-trifluoromethyl-.beta.uridine characterized in that a 5-trifluoromethyl-2,4-bis(triorganosilyloxy)pyrimidine and a 1-halogeno-2-deoxy-.alpha.-D-erythro-pentofuranose derivative are subjected to condensation reaction in chloroform to give a 1-(2-deoxy-.beta.-D-erythro-pentofuranoxyl)-5-trifluoromethyluracil derivative which is then subjected to the deprotection reaction to give 2'-deoxy-5-trifluoromethyl-.beta.-uridine.

REFERENCES:
patent: 4092472 (1978-05-01), Townsend et al.
patent: 4211773 (1980-07-01), Lopez et al.
patent: 4352795 (1982-10-01), Cook
patent: 4760137 (1988-07-01), Robins et al.
patent: 4898936 (1990-02-01), Ollmann et al.
patent: 4914028 (1990-03-01), Hertel et al.
Lawlor et al., Chemical Abstracts vol. 99: 97963g, (1983).
Bardos T. J. et al, Tetrahedron Letters, No. 16, 1966 pp. 1759-1764 "Stereoselective Synthesis of Anomeric 5-Mercapto-2-Deoxyuridines".
The Synthesis of 2-Deoxy-5-Trifluoromethyl uridine utilizing a coupling reaction; Kawakami et al.; Heterocycles, vol. 31; No. 3, 1990; pp. 569-574.

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