反应详情

(2R,3S,4R,5R)-2-(6Amino-9H-purin-9-yl)-5-{[(triisopropylsilyl)oxy]methyl}-tetrahydrofuran-3,4-diyl diacetate (0.605 g, 1.19 mmol) was dissolved in dibromomethane (24 mL). Trimethylsilyl bromide (0.17 mL, 1.35 mmol) was added dropwise followed by tert-butylnitrite (0.97 mL, 8.12 mmol). The orange solution was stirred for 2.5 hours then slowly poured into a 1:1 mixture of saturated sodium bicarbonate and dichloromethane and extracted. The pale yellow organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated. The yellow solid was purified by flash chromatography eluting with 25% ethyl acetate/hexanes to give the title compound as a yellow solid (0.402 g, 52%).

1. extractionextracted
2. washThe pale yellow organic layer was washed with water and brine
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe yellow solid was purified by flash chromatography
7. washeluting with 25% ethyl acetate/hexanes