반응 #76832

반응 방정식

(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

용매

pyridine

dichloromethane

pyridine

반응 조건

후처리

1. 1
   workup.WAITat 5° C. for 2 hr
2. 2
   workup.WAITAfter 30 min at 5° C.
3. 3
   추출extracted with dichloromethane
4. 4
   기타The organic phase was dried
5. 5
   기타the product purified by silica ge column chromatography with stepwise increasing MeOH
6. 6
   세척eluting with 3.5% MeOH in CH2Cl2 (Yield 2.7 g)

실험 절차

(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).

출처