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

HRID 54636노트

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HRID 54636 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-764afb4f4adc45c882af92922ad7a2cc
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623070

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