반응 #6365

반응 방정식

diethyl azodicarboxylate

diethyl (R)-[2-benzyloxy-1-(hydroxymethyl)ethoxy]methylphosphonate

triphenylphosphine

2-[bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurine

→

(S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine

수율 88.6%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITleft
3. 3
   기타The solvent was evaporated under reduced pressure
4. 4
   기타the residue obtained
5. 5
   기타chromatographed on silica gel

실험 절차

To a stirred solution of diethyl (R)-[2-benzyloxy-1-(hydroxymethyl)ethoxy]methylphosphonate (1.0 g, 3 mmol), triphenylphosphine (1.18 g, 4.5 mmol) and 2-[bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurine (1.15 g, 3 mmol) in dry THF (20 ml), cooled in ice and under a mitrogen atmosphere, was added, dropwise, diethyl azodicarboxylate (0.71 ml, 4.5 mmol). The resulting solution was allowed to warm to ambient temperature and left stirring for 16 hours. The solvent was evaporated under reduced pressure and the residue obtained chromatographed on silica gel using hexane/ethyl acetate 2:1 as eluant. The eluant was changed as follows: hexane/ethyl acetate 1:1, hexane/ethyl acetate 1:2 and finally to ethyl acetate to give (S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine as a colourless oil (1.85 g, 88%).

출처