反応 #89005
ord-1a5264f6007c4e27a466706e68b89a45
反応方程式
反応物
試薬
溶媒
反応条件
後処理
- 1workup.ADDITIONwas added BSA (630 mg, 3 mmol)
- 2その他The resulting reaction mixture
- 3その他to form a clear solution
- 4温度After the solution was cooled to room temperature
- 5温度After being heated at 70° C. for 14 hours
- 6その他the solvent was removed in vacuo
- 7その他The residue was partitioned between EtOAc and saturated NaHCO3 solution (30 mL)
- 8その他The organic layer was separated
- 9抽出the aqueous phase was extracted with EtOAc (30 mL) twice
- 10洗浄The combined organic layers were washed with brine
- 11乾燥dried over Na2SO4
- 12濃縮concentrated in vacuo
実験手順
To a suspension of 5-amino-3,6-dihydrothiazolo[4,5-d]pyrimidine-2,7-dione (186 mg, 1 mmol) in ACN (10 mL) was added BSA (630 mg, 3 mmol). The resulting reaction mixture was then stirred at 70° C. under argon for 0.5 hour to form a clear solution. After the solution was cooled to room temperature, 1-[(2S,4R)-4-azido-5-methoxy-tetrahydrofuran-2-yl]ethyl benzoate (compound 25k, 300 mg, 1.0 mmol) and TMSOTf (1.15 g, 5 mmol) were added in sequence. After being heated at 70° C. for 14 hours, the solvent was removed in vacuo. The residue was partitioned between EtOAc and saturated NaHCO3 solution (30 mL). The organic layer was separated and the aqueous phase was extracted with EtOAc (30 mL) twice. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford 600 mg crude product of 1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-azido-tetrahydrofuran-2-yl]ethyl benzoate (compound 25l), which was used in next step without further purification. MS obsd. (ESI+) [(M+H)+]: 442.