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Imidazole → 6-O-(4,4'-dimethoxytrityl)-3-O-(2-fluoroethyl)-4-O-(triethylsilyl)-2-deoxy-2-(thymin-1yl)-D-altro-hexitol

HRID 43300
ノート
印刷プレビュー

反応式

HRID 43300 の反応式
[CH3:1][O:2][C:3]1[CH:46]=[CH:45][C:6]([C:7]([O:22][CH2:23][C@@H:24]([OH:44])[C@@H:25]([OH:43])[C@@H:26]([O:39][CH2:40][CH2:41][F:42])[C@H:27]([N:30]2[CH:38]=[C:36]([CH3:37])[C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:28][OH:29])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.N1C=CN=C1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl[Si:67]([CH2:72][CH3:73])([CH2:70][CH3:71])[CH2:68][CH3:69]>CN(C=O)C.CCOC(C)=O>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([O:22][CH2:23][C@@H:24]([OH:44])[C@@H:25]([O:43][Si:67]([CH2:72][CH3:73])([CH2:70][CH3:71])[CH2:68][CH3:69])[C@@H:26]([O:39][CH2:40][CH2:41][F:42])[C@H:27]([N:30]2[CH:38]=[C:36]([CH3:37])[C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:28][OH:29])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]2[CH:45]=[CH:46][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 14812Phosphorus oxide (P4O10)HCID 866614446-O-(4,4'-dimethoxytrityl)-2-deoxy-2(thymin-1yl]-3-O-(2-fluoroethyl)D-altro-hexitol

生成物 1

HCID 866614466-O-(4,4'-dimethoxytrityl)-3-O-(2-fluoroethyl)-4-O-(triethylsilyl)-2-deoxy-2-(thymin-1yl)-D-altro-hexitol収率 82.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Compound 6, prepared as per the procedures illustrated in Example 13 (2.50 g, 4.00 mmol) was mixed with imidazole (1.36 g, 20.0 mmol) over P2O5 under reduced pressure. This mixture was dissolved in anhydrous DMF (13 mL) and chloro triethylsilane (1.71 mL, 10 mmol) was added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted in EtOAc (100 mL), washed with sat. NaHCO3 (100 mL) and brine (50 mL) then dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography (50% EtOAc in hexanes) to yield Compound 8 (2.45 g, 82.5%) as a white foam. MS (ES): m/z 760.2 [M+Na]+.

後処理

  1. washwashed with sat. NaHCO3 (100 mL) and brine (50 mL)
  2. dry with materialthen dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-f76691064f6648a099b401fbe0225912
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08536320B2

反応ノート

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