Dicyclohexylcarbodiimide → 2',3'-dideoxy-3'-fluoro-5'-O-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyl]guanosine

HRID 1790813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1790813
[C:1]([NH:20][C@H:21]([C:25]([O:27][CH2:28][CH:29]([CH2:36][O:37][C:38](=[O:56])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:26])[CH:22]([CH3:24])[CH3:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:57][C@@H:58]1[C@@H:62]([CH2:63]O)[O:61][C@@H:60]([N:65]2[C:75]3[N:74]=[C:72]([NH2:73])[NH:71][C:69](=[O:70])[C:68]=3[N:67]=[CH:66]2)[CH2:59]1.CN(C1C=CC=CN=1)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[F:57][C@@H:58]1[C@@H:62]([CH2:63][O:34][C:33](=[O:35])[CH2:32][CH2:31][CH2:30][CH:29]([CH2:28][O:27][C:25](=[O:26])[C@H:21]([CH:22]([CH3:24])[CH3:23])[NH:20][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:36][O:37][C:38](=[O:56])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[O:61][C@@H:60]([N:65]2[C:75]3[N:74]=[C:72]([NH2:73])[NH:71][C:69](=[O:70])[C:68]=3[N:67]=[CH:66]2)[CH2:59]1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 154851735-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoic acidHCID 1354318173'-Fluoro-2',3'-dideoxyguanosine

Produkt 1

HCID 1361217062',3'-dideoxy-3'-fluoro-5'-O-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyl]guanosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoic acid (462 mg, 0.6 mmole) and 2′,3′-dideoxy-3′-fluoroguanosine (340 mg, 1.25 mmol) in DMF (3 ml) were added dimethylaminopyridine (7 mg, 0.06 mmole), and DCC (136 mg, 0.66 mmol). The reaction was kept at room temperature overnight, and then at 40° C. for two hours. The reaction mixture was filtered through Celite and poured into dichloromethane, and washed with aqueous sodium hydrogen carbonate solution. The product 2′,3′-dideoxy-3′-fluoro-5′-O-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyl) guanosine was isolated by silica gel column chromatography. (93 mg)

Aufarbeitung

  1. waitat 40° C. for two hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. additionpoured into dichloromethane
  4. washwashed with aqueous sodium hydrogen carbonate solution

Quellen und Nachweise

ORD-Eintrag
ord-2a1842918cfe48009ac4bd036a2c86d6
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071173B2

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