Acetone → 3-(5,6-Dihydroxyhexyl)-1-methylthymine

Participants

Reaction Steps

A solution of 3-(5-hexenyl)-1-methylthymine (2.00 g, 9 mmol), 4-methylmorpholine-N oxide (1.17 mg, 10 mmol), and a 2.5% sol. in t-butanol of osmium tetroxide (0.15 mL) in acetone (15 mL) and water (10 mL) was stirred for 20 hours. After addition of a saturated solution of sodium hydrosulfite (10 mL) and 15 minutes of stirring, the reaction mixture was extracted with 20% ethanol/dichloromethane (4×40 mL). The combined organic layers were dried over sodium sulfate and the solvent evaporated under vacuum to a give white solid residue. The solid was recrystallized in ethanol to yield 2.00 g (89%) of 3-(5,6-dihydroxyhexyl)-1-methylthymine (inventive compound no. 1907).

Provenance & Evidence