反应详情

A catalytic amount of ammonium sulfate was added to a mixture of 6-chloropurine (0.56 grams, 3.62 mmol) and hexamethyldisilazane (15 mL), and the mixture was refluxed for 3 hours. The solvent was evaporated under reduced pressure, and the residue was co-evaporated with dry toluene (3×10 mL). The white solid residue was dissolved in dry methylene chloride (40 mL) and 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-ribofuranose, (1.00 g, 3.10 mmol) was added. After 10 minutes of stirring, trimethylsilyl triflate (0.8 mL) was added, and the solution stirred at room temperature for an additional 3 hours. A solution of cold, saturated sodium bicarbonate was added. After 5 minutes stirring, the organic layer was separated and the aqueous solution extracted with methylene chloride (2×30 mL). The organic layers were combined and dried over sodium sulfate, to give (5S,2R,3R)-2-(6-chloropurin-9-yl)-5-(phenylcarbonyloxymethyl)oxolan-3-yl acetate, which was purified by crystallization from methanol. The mother liquor was chromatographed on a Chromatotron, to provide additional product.

1. temperaturethe mixture was refluxed for 3 hours
2. customThe solvent was evaporated under reduced pressure
3. dissolutionThe white solid residue was dissolved in dry methylene chloride (40 mL)
4. stirringthe solution stirred at room temperature for an additional 3 hours
5. stirringAfter 5 minutes stirring
6. customthe organic layer was separated
7. extractionthe aqueous solution extracted with methylene chloride (2×30 mL)
8. dry with materialdried over sodium sulfate