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Hydrogen Peroxide → HCID 67530779, 화합물

HRID 2389113
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HRID 2389113 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21]([C@:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:29])[CH2:27][OH:28])[CH:20]=[CH:19]3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=NN=N1.[O:43]1CCCC1.C(N(CC)[P:51]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])C.OO>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21]([C@:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:29])[CH2:27][O:28][P:51]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])([O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:43])[CH:20]=[CH:19]3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 67531733HCID 67531733, 화합물HCID 178418441HCID 178418441, 화합물

생성물 1

HCID 67530779HCID 67530779, 화합물수율 101.9%

실험 절차

To a solution of (R)-tert-butyl 2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-1-hydroxypropan-2-ylcarbamate (20.0 mg, 0.0000388 mol) and 1H-tetrazole (30.4 mg, 0.000434 mol) in tetrahydrofuran (2 mL, 0.02 mol) was added di-tert-butyl N,N-diethylphosphoramidite (60.1 μL, 0.000216 mol) at room temperature. The resulting mixture was stirred at room temperature overnight, then hydrogen peroxide (180 μL, 0.0017 mol) was added and the mixture was stirred at room temperature for 1 h. The reaction was quenched with saturated. Na2S2O3, then extracted with EtOAc, and dried over Na2SO4. The residue was chromatographed with MeOH—CH2Cl2 (0-20%) to give (R)-tert-butyl 2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-1-(di-tert-butoxyphosphoryloxy)propan-2-ylcarbamate as a gel (28 mg, 100%).

후처리

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. customThe reaction was quenched with saturated
  3. extractionNa2S2O3, then extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe residue was chromatographed with MeOH—CH2Cl2 (0-20%)

출처 및 근거

ORD 기록
ord-1687eed6fcdc48edb528db590e21c3b0
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08269043B2

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