反応 #76832

反応方程式

(R)-9-[2-Hydroxymethyl 4-(t-butyldiphenylsilyloxy)butyl]guanine

sodium hydrogen carbonate

stearoyl chloride

methanol

stearoyl chloride

→

(R)-9-[2-(Stearoyloxymethyl)-4-(t-butyldiphenylsilyloxy)butyl]guanine

溶媒

pyridine

dichloromethane

pyridine

反応条件

後処理

1. 1
   workup.WAITat 5° C. for 2 hr
2. 2
   workup.WAITAfter 30 min at 5° C.
3. 3
   抽出extracted with dichloromethane
4. 4
   その他The organic phase was dried
5. 5
   その他the product purified by silica ge column chromatography with stepwise increasing MeOH
6. 6
   洗浄eluting with 3.5% MeOH in CH2Cl2 (Yield 2.7 g)

実験手順

(R)-9-[2-Hydroxymethyl 4-(t-butyldiphenylsilyloxy)butyl]guanine (2.31 g, 5 mmole) was coevaporated with dry pyridine twice and dissolved in pyridine (20 ml). To the solution was slowly added dropwise stearoyl chloride (1.86 ml, 5.5 mmole, technical grade) in dichloromethane (2 ml) at −5° C. The reaction was kept at the same temperature for 1 hr and then at 5° C. for 2 hr. The reaction was monitored by TLC. Additional stearoyl chloride (0.29 ml) at −5° C. was added due to incompletion of reaction. After 30 min at 5° C., methanol (3 ml) was added and the reaction mixture stirred for 20 min. It was then poured into aqueous sodium hydrogen carbonate solution, and extracted with dichloromethane. The organic phase was dried and the product purified by silica ge column chromatography with stepwise increasing MeOH, eluting with 3.5% MeOH in CH2Cl2 (Yield 2.7 g).

出典