Triethylamine → Thymine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3'-O-β-butyldimethylsilyl-4'-hydroxymethyl-β-D-erythro-pentofuranosylthymine (1.2 g, 3.1 mM), prepared, e.g., as described in Preparation 4, in CH2Cl2 (20 ml), triethylamine (0.6 g. 6 mM) was added followed by the dropwise addition of mesyl chloride (0.340 g, 3 mM), while the solution was stirred at 24° C. The solution was concentrated by the removal of the solvent by evaporation. The residue was flash chromatographed on silica gel eluting by CH2Cl2 with 5% methanol, to give a mixture of the 4'-α and 4'-β isomers of 3'-O-t-butyldimethylsilyl-4'-methanesulfonyloxymethylthymidine (1.1 g, 2.4 mM). Calcd. for C18H32N2O8Si: C, 46.53; H, 6.94; N, 6.05. Found: C, 46.90; H, 7.02; N, 5.78.

Provenance & Evidence