Chlorotrimethylsilane → HCID 11146723, compound

Participants

Reaction Steps

Dried 5′-O-t-butyldiphenylsilyl-2′-O-(hydroxyethyl)-adenosine (24 g, 43.7 mmol) was dissolved in anhydrous pyridine (500 mL) under inert atmosphere, and trimethylchlorosilane (27.7 mL, 218 mmol) was added at 0° C. The reaction was allowed to warm to ambient temperature, stirred for 1 hour, then cooled to 0° C. Benzoyl chloride (25.3 mL, 218 mmol) was added dropwise, then the reaction was allowed to warm to ambient temperature and stirred for 4 hours after which it was cooled to 0° C. and water (100 mL) was added. After stirring for 10 minutes aqueous 30% NH4OH (100 mL) was added, and the reaction was stirred at 0° C. for 1 hour. The solvent was evaporated in vacuo to give a residue which was dissolved in EtOAc (1 L), and the resulting solution was washed with water (200 mL) twice, then with brine (100 mL). The organic solution was dried with MgSO4, and the solvent was evaporated in vacuo to give a residue. The residue was purified by column chromatography using CH2Cl2-EtOAc-MeOH, 70:27:3, to give the title compound as a solid (23.77 g, 83%).

Provenance & Evidence