반응 #576261

반응 방정식

DCC

2′,3′-dideoxy-3′-fluoro-5′-O-[3-(1,3-dihydroxy-2-propyloxy carbonyl)-propanoyl]guanosine

N-CBZ-L-valine

HOBT

→

2′,3′-dideoxy-3′-fluoro-5′-O-{3-[1-(N-CBZ-L-valyloxy)-3-hydroxy-2-propyloxy carbonyl]-propanoyl}guanosine

용매

DMF

반응 조건

후처리

1. 1
   여과The mixture was filtered
2. 2
   기타the solution evaporated under reduced pressure
3. 3
   workup.ADDITIONEthyl acetate (150 ml) was added
4. 4
   세척the organic phase washed twice with 5% acetic acid, 5% sodium hydrogen carbonate and water
5. 5
   건조The organic phase was dried with sodium sulfate
6. 6
   기타evaporated under reduced pressure
7. 7
   기타The product was isolated by silica gel column chromatography

실험 절차

A mixture of 2′,3′-dideoxy-3′-fluoro-5′-O-[3-(1,3-dihydroxy-2-propyloxy carbonyl)-propanoyl]guanosine (1.3 g, 2.93 mmole), N-CBZ-L-valine (1.00 g, 4 mmole), HOBT (0.54 g, 4 mmole) and DMAP (48.8 mg, 0.4 mmole) was coevaporated two times with DMF and reduced to about 60 ml. DCC (0.91 g, 4.4 mmole) was added and the mixture was stirred for 72 hours at room temperature. The mixture was filtered and the solution evaporated under reduced pressure. Ethyl acetate (150 ml) was added and the organic phase washed twice with 5% acetic acid, 5% sodium hydrogen carbonate and water. The organic phase was dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography. Yield: 0.99 g

출처