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5’-O-Trityluridine-2’,3’-lyxo-epoxide synthesis

4synthesis methods
-

Yield:96253-10-0 91%

Reaction Conditions:

with sodium hydroxide in water;acetone at 20; for 18 h;

Steps:

4.6. 1-(5-Ethynylfuran-2-yl)pyrimidine-2,4(1H,3H)-dione (9)

General procedure: The di-O-mesyl compound 7 (7.88 g, 20.0 mmol) was dissolved in 1 M NaOH in acetone/water (1:1) (40 mL). The resulting solution was kept at room temperature for 18 h, and then poured in ice-water mixture (500 mL) neutralized with 1 M HCl. The resulting precipitate was filtered off and purified by column chromatography on silica gel using CH2Cl2/EtOAc (3:2), as eluent. The appropriate fractions were pooled and the solvent was evaporated, recrystallized form ethanol/petroleum ether (1:2, v/v) to give 9 (3.50 g, 86.6%), as white solid

References:

Amin, Mahmoud A. [Tetrahedron,2011,vol. 67,# 9,p. 1703 - 1708] Location in patent:experimental part