Azobisisobutyronitrile → 3'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-C-Allylthymidine

HRID 1955834ノート

反応式

HRID 1955834 の反応式
[Si:1]([O:18][C@@H:19]1[C@@H:23]([CH2:24]I)[O:22][C@@H:21]([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([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.[CH3:35][C:36](N=NC(C#N)(C)C)(C#N)[CH3:37]>C1(C)C=CC=CC=1>[Si:1]([O:18][C@@H:19]1[C@@H:23]([CH2:24][CH2:37][CH:36]=[CH2:35])[O:22][C@@H:21]([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([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

参加物

4

反応物 2

HCID 6547AzobisisobutyronitrileHCID 109300073'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-Iodothymidine

生成物 1

HCID 186587093'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-C-Allylthymidine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
65 °C

実験手順

A stirred solution of 3'-O-(t-butyldiphenylsilyl)-5'-deoxy-5'-iododthymidine (12, 1.77 g, 3 mmol), allytributyltin (2.97 g, 9 mmol) and AIBN (0.54 g, 3.3 mmol) in dry toluene (30 ml) was degassed completely and heated at 65° C. for 6 hr. The solution was cooled and concentrated under vacuo. The residue was purified by silica gel column chromatography and on elution with hexanes:EtOAc (1:1, v/v) furnished the title compound as homogeneous material. Appropriate fractions were pooled and evaporated to furnish 46, 0.75 g of a white foam, 50% yield. The structure was confirmed by 1H NMR.

後処理

  1. temperatureThe solution was cooled
  2. concentrationconcentrated under vacuo
  3. customThe residue was purified by silica gel column chromatography and on elution with hexanes:EtOAc (1:1

出典と根拠

ORDレコード
ord-43b4f9dea03b4dcbb624790e1ced8a4d
出典データセット
uspto-grants-1998_07
特許番号
US05777092

反応ノート

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