Trityl chloride → 2'-Deoxy-5'-O-(triphenylmethyl)uridine

HRID 467262

反応式

HRID 467262 の反応式
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:17]([O:7][CH2:6][C@H:5]1[O:8][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2][C@@H:3]1[OH:4])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

4

反応物 2

HCID 6456Trityl chlorideHCID 13712Deoxyuridine

生成物 1

HCID 137119602'-Deoxy-5'-O-(triphenylmethyl)uridine収率 93%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

A solution of (50 g, 0.22 mole) of 2'-deoxyuridine and 62 g (0.22 mole) of trityl chloride in 350 ml of dry pyridine was placed in a preheated (100° C.) flask and stirred at 100° C. under an air condenser for two hours. The reaction mixture was cooled to room temperature and slowly poured into 4 L of vigorously stirred ice-water. The solid obtained was filtered, washed with water until free from pyridine, and dissolved in chloroform and dried (Na2SO4 or MgSO4). Filtration and evaporation of chloroform yielded the 5'-O-trityl-2'-deoxyuridine product as an syrup (96 g, 93%), which was used for the next reaction without further purification.

後処理

  1. customwas placed in a preheated (100° C.) flask
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe solid obtained
  4. filtrationwas filtered
  5. washwashed with water until free from pyridine
  6. dissolutiondissolved in chloroform
  7. dry with materialdried (Na2SO4 or MgSO4)
  8. filtrationFiltration and evaporation of chloroform

出典と根拠

ORDレコード
ord-6ef9de1aee954a7c83dae1eb2677ac77
出典データセット
uspto-grants-1992_10
特許番号
US05159067

関連ノート

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