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

HRID 989994ノート

反応式

HRID 989994 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-888e98b0d0b1421b9d92200c75ea5763
出典データセット
uspto-grants-2002_10
特許番号
US06458772B1

反応ノート

読み込み中…