Pyridine → 2',3'-Dideoxy-3'-fluoro-5'-O-[3-(N-CBZ-L-valyloxymethyl)-4-stearoyloxy-butoxycarbonyl] guanosine

HRID 489073Notes

Reaction equation

HRID 489073 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[CH2:3]1.N1C=CC=CC=1.[C:26]([NH:36][C@H:37]([C:41]([O:43][CH2:44][CH:45]([CH2:52][O:53][C:54](=[O:72])[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[CH2:46][CH2:47][O:48][C:49](Cl)=[O:50])=[O:42])[CH:38]([CH3:40])[CH3:39])([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>CN(C=O)C.ClCCl>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:49]([O:48][CH2:47][CH2:46][CH:45]([CH2:44][O:43][C:41](=[O:42])[C@H:37]([CH:38]([CH3:40])[CH3:39])[NH:36][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:52][O:53][C:54](=[O:72])[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])=[O:50])[O:5][C@@H:4]([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[CH2:3]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 233875313-(N-CBZ-L-valyloxymethyl)-4-stearoyloxy-butoxycarbonyl chlorideHCID 1354318173'-Fluoro-2',3'-dideoxyguanosine

Product 1

HCID 1360053542',3'-Dideoxy-3'-fluoro-5'-O-[3-(N-CBZ-L-valyloxymethyl)-4-stearoyloxy-butoxycarbonyl] guanosine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2′,3′-dideoxy-3′-fluoroguanosine (269 mg, 1.0 mmole in absolute DMF were added pyridine (198 mg, 2.5 mmole) and a solution of 3-(N-CBZ-L-valyloxymethyl)-4-stearoyloxy-butoxycarbonyl chloride (750 mg, 1.1 mmole) in 5 ml dichloromethane. The mixture was stirred for three days at room temperature. The solution was evaporated under reduced pressure and the product was isolated by silica gel column chromatography. Yield: 120 mg

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customthe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-f3dd2e97aaea4580b83b94080b3a5903
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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