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

HRID 467262

반응식

HRID 467262 반응식
[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

참가 물질

4

반응물 2

HCID 6456Trityl chlorideHCID 13712Deoxyuridine

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6ef9de1aee954a7c83dae1eb2677ac77
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05159067

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