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Magnesium trifluoromethanesulfonate → (S)-Methyl 3-((S)-1-(tert-butyldimethylsilyloxy)propan-2-yloxy)-2-hydroxypropanoate

HRID 1098218
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HRID 1098218 반응식
FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=O.[O:18]1[CH2:20][C@H:19]1[C:21]([O:23][CH3:24])=[O:22].[Si:25]([O:32][CH2:33][C@@H:34]([OH:36])[CH3:35])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CCOC(C)=O>[Si:25]([O:32][CH2:33][C@@H:34]([O:36][CH2:20][C@H:19]([OH:18])[C:21]([O:23][CH3:24])=[O:22])[CH3:35])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]
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참가 물질

5

반응물 3

HCID 2734125Magnesium trifluoromethanesulfonateHCID 10942355Methyl (2S)-2-oxiranecarboxylateHCID 13175136(S)-1-((Tert-butyldimethylsilyl)oxy)propan-2-OL

생성물 1

HCID 86640846(S)-Methyl 3-((S)-1-(tert-butyldimethylsilyloxy)propan-2-yloxy)-2-hydroxypropanoate수율 37.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate
용매

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온도
10 °C

실험 절차

Magnesium trifluoromethanesulfonate (0.974 g, 3.02 mmol) was added in one portion to (S)-methyl oxirane-2-carboxylate (1.234 g, 12.08 mmol) and (S)-1-(tert-butyldimethylsilyloxy)propan-2-ol (CAS no. 113534-13-7) (2.30 g, 12.08 mmol) in EtOAc (5 mL) cooled to 10° C. The resulting suspension was stirred at 10° C. for 10 minutes and then warmed to 45° C. and stirred for 2 days. The crude product was purified by flash silica chromatography, eluting with 0 to 30% EtOAc in isohexane to afford the product (1.336 g, 37.8%). 1H NMR (400 MHz, DMSO) δ0.00 (s, 6H), 0.83 (s, 9H), 0.98 (d, 3H), 3.34-3.53 (m, 3H), 3.55-3.64 (m, 5H), 4.11 (q, 1H), 5.39 (d, 1H)

후처리

  1. temperaturewarmed to 45° C.
  2. stirringstirred for 2 days
  3. customThe crude product was purified by flash silica chromatography
  4. washeluting with 0 to 30% EtOAc in isohexane

출처 및 근거

ORD 기록
ord-def69126da904439adb9a57acd51ca11
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143263B2

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