Реакция #76832

Уравнение реакции

(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

Растворители

pyridine

dichloromethane

pyridine

Условия реакции

Обработка

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

Методика

(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).

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