Trimethylsilyl triflate → 9-((4s,5s)-4-Azido-5-((tert-butyldimethylsilyloxy)methyl)tetrahydrofuran-2-yl)-6-chloro-9h-purin-2-amine

温度

85 °C

A suspension of 1-((2R,4S,5S)-4-azido-5-((tert-butyldimethylsilyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H, 3H)-dione, 75 (TBS protected AZU)1 (0.2 g, 0.544 mmol) and 2-amino-6-chloropurine (0.25 g, 1.51 mmol) in acetonitrile (6 mL) was added BSA (2 ml, 1.51 mmol). The reaction mixture was heated to 85° C. for 30 min, then cooled to 0° C. TMSOTf (0.51 mL) was added. The reaction mixture was heated to 85° C. overnight, cooled to room temperature, poured into saturated sodium bicarbonate, extracted with ethyl acetate (20 mL×2), dried, conc., and purified by flash column chromatography with ethyl acetate:hexane=1:1 to get the desired compound 0.1 g. 43%. It contained two isomers (alpha:beta=1.1:1)

1. additionwas added BSA (2 ml, 1.51 mmol)
2. temperaturecooled to 0° C
3. temperatureThe reaction mixture was heated to 85° C. overnight
4. temperaturecooled to room temperature
5. extractionextracted with ethyl acetate (20 mL×2)
6. customdried
7. customconc., and purified by flash column chromatography with ethyl acetate

ORDレコード

ord-a6556d6e20e74f10a54dcc307dabf09e

出典データセット

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08815829B2