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Trimethylsilyl triflate → 4-Chloro-1-(2-O-methyl-3,5-di-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

HRID 2210631
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HRID 2210631 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]CC[Si](C)(C)C)[N:3]=1.[CH3:15][O:16][C@@H:17]1[C@H:30]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:29]([CH2:40][O:41][C:42](=[O:49])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:28][C@@H:18]1OC(=O)C1C=CC=CC=1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C@@H:18]2[O:28][C@H:29]([CH2:40][O:41][C:42](=[O:49])[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@@H:30]([O:31][C:32](=[O:39])[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C@H:17]2[O:16][CH3:15])[C:4](=[O:8])[N:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 65367Trimethylsilyl triflateHCID 102632784-Chloro-2-(2-trimethylsilanyl-ethoxy)-pyrimidineHCID 10917755(-)-Inosine Dehydroxy-N-(6-iminohexyl)-2,2,2-trifluoroacetamide

생성물 1

HCID 217824984-Chloro-1-(2-O-methyl-3,5-di-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one수율 91%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

4-Chloro-2-trimethylsilylethoxy-pyrimidine (3.5 g, 15.2 mmole) and 2-O-methyl-1,3,5-tri-O-benzoyl-α-D-ribose (7.0 g, 15.2 mmole) were dissolved in acetonitrile (100 ml). This solution was treated with trimethylsilyl trifluoromethanesulfonate (2.8 g, 15.2 mmole) and stirred for 1.5 hours. The reaction mixture was concentrated to an oil and redissolved in 300 ml CH2Cl2. The CH2Cl2 solution was washed with cold concentrated sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated to an oil. The oil was coevaporated with acetonitrile and dried to a brown foam to give 6.70 g (91%) crude product.

후처리

  1. concentrationThe reaction mixture was concentrated to an oil
  2. dissolutionredissolved in 300 ml CH2Cl2
  3. washThe CH2Cl2 solution was washed with cold concentrated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil
  7. customdried to a brown foam

출처 및 근거

ORD 기록
ord-28f666b72fb4495ba2c9b198afa6f7c7
출처 데이터셋
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05459243

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