Tetrabutylammonium Fluoride → 2'-Deoxy-5-ethynyl-5'-O-[(4-methoxyphenyl)(diphenyl)methyl]uridine

Participants

Reaction Steps

1.40 g of 2′-deoxy-5-[(trimethylsilyl)ethynyl]-5′-O-(4-methoxytrityl)-uridine (2.35 mmole) prepared in 1-2) was dissolved in 20 ml of THF, and then 0.95 ml TBAF (1.4 eq) was added thereto. After 7 hours, the reaction was terminated, THF was removed using a rotary evaporator, and the resulting residue was subjected to column chromatography (silica gel 60, 230-400 meshes, Merck) to obtain the title compound as a solid. The chromatography was conducted using a mixture of CH2Cl2 and methanol as an eluting solution whose mix ratio was gradually varied from 100:1 to 50:1 (v/v).

Provenance & Evidence