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Chlorotrimethylsilane → 1-(2,3,5-Tri-O-benzoyl-beta-L-ribofuranosyl)-N4-acetylcytosine

HRID 744164
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HRID 744164 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][NH:8][C:7](=[O:11])[N:6]=1)(=[O:3])[CH3:2].C(O[C@H:16]1[O:38][C@@H:37]([CH2:39][O:40][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:17]1[O:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)C.C[Si](N[Si](C)(C)C)(C)C.Cl[Si](C)(C)C.Cl[Sn](Cl)(Cl)Cl>CC#N>[C:19]([O:18][C@H:17]1[C@@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:37]([CH2:39][O:40][C:41](=[O:48])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:38][C@@H:16]1[N:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:6][C:7]1=[O:11])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 24287Tin tetrachlorideHCID 10973190Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 178474340HCID 178474340, 화합물

생성물 1

HCID 540996081-(2,3,5-Tri-O-benzoyl-beta-L-ribofuranosyl)-N4-acetylcytosine
수율 70%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of N4 -acetylcytosine (0.18 g, 1.19 mmol) and compound 2 (0.50 g, 0.99 mmol) in anhydrous MeCN (30 ml) were successively added HMDS (0.17 ml, 0.79 mmol), ClSiMe3 (0.10 ml, 0.79 mmol) and SnCl4 (0.14 ml, 1.19 mmol). The resulting clear solution was refluxed for one hour. Then the solvent was evaporated and the residue dissolved in EtOAc (100 ml), washed with NaHCO3 and H2O. After evaporation of the solvent the residue was purified on a silica gel column using EtOAc/petroleum ether (70%) to give pure 7 (0.41 g, 70%) as a white foam.

후처리

  1. temperatureThe resulting clear solution was refluxed for one hour
  2. customThen the solvent was evaporated
  3. dissolutionthe residue dissolved in EtOAc (100 ml)
  4. washwashed with NaHCO3 and H2O
  5. customAfter evaporation of the solvent the residue
  6. customwas purified on a silica gel column

출처 및 근거

ORD 기록
ord-9ff09d7a3542454a9c86c5987fa969ca
출처 데이터셋
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05559101

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