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Peracetic Acid → 17-Ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-(6'"-tert-butyldimethylsilyloxynaphth-2-yloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetra-methyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]-octacos-18-ene-2,3,10,16-tetraone

HRID 2082628
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인쇄 미리보기

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HRID 2082628 반응식
[Si](OC1C=C2C(=CC=1)C=C([Bi](C1C=CC3C(=CC=C(O[Si](C(C)(C)C)(C)C)C=3)C=1)C1C=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])(C)[CH3:32])[CH:26]=3)C=1)C=C2)(C(C)(C)C)(C)C.[C:56](OO)(=O)C.[CH2:61]1[CH2:65]OC[CH2:62]1.[CH2:66]([CH:68]1[CH:94]=[C:93]([CH3:95])[CH:92]([F:96])[CH:91]([CH3:97])[CH2:90][CH:89]([O:98][CH3:99])[CH:88]2[O:100][C:84]([OH:104])([CH:85]([CH3:103])[CH2:86][CH:87]2[O:101][CH3:102])[C:83](=[O:105])[C:82](=[O:106])[N:81]2[CH:76]([CH2:77][CH2:78][CH2:79][CH2:80]2)[C:75](=[O:107])[O:74][CH:73]([C:108]([CH3:119])=[CH:109][CH:110]2[CH2:115][CH2:114][CH:113]([OH:116])[CH:112]([O:117][CH3:118])[CH2:111]2)[CH:72]([CH3:120])[CH:71]([OH:121])[CH2:70][C:69]1=[O:122])[CH3:67]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:66]([CH:68]1[CH:94]=[C:93]([CH3:95])[CH:92]([F:96])[CH:91]([CH3:97])[CH2:90][CH:89]([O:98][CH3:99])[CH:88]2[O:100][C:84]([OH:104])([CH:85]([CH3:103])[CH2:86][CH:87]2[O:101][CH3:102])[C:83](=[O:105])[C:82](=[O:106])[N:81]2[CH:76]([CH2:77][CH2:78][CH2:79][CH2:80]2)[C:75](=[O:107])[O:74][CH:73]([C:108]([CH3:119])=[CH:109][CH:110]2[CH2:115][CH2:114][CH:113]([O:116][C:61]3[CH:65]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:30][Si:31]([C:34]([CH3:35])([CH3:37])[CH3:36])([CH3:32])[CH3:56])[CH:26]=4)[CH:62]=3)[CH:112]([O:117][CH3:118])[CH2:111]2)[CH:72]([CH3:120])[CH:71]([OH:121])[CH2:70][C:69]1=[O:122])[CH3:67]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6585Peracetic AcidHCID 8028TetrahydrofuranHCID 21469196Tri(6-tert-butyldimethylsilyloxynaphth-2-yl)bismuthineHCID 5702442717-Ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13, 19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo-[22.3.1.04,9]octacos-18-ene2,3,10,16-tetraone

생성물 1

HCID 57108327
17-Ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-(6'"-tert-butyldimethylsilyloxynaphth-2-yloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetra-methyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]-octacos-18-ene-2,3,10,16-tetraone

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

To a stirred solution of tris(6-tert-butyldimethylsilyloxynaphth-2-yl)bismuthine (100 mg, 0.215 mmol) in CH2Cl2 (4 mL) is added peracetic acid (0.05 mL, 0.238 mmol, 32 wt % in dilute acetic acid). To this stirred solution is added THF (1 mL), 17-ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13, 19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo-[22.3.1.04,9 ]octacos-18-ene2,3,10,16-tetraone (100 mg, 0.126 mmol) and Cu(OAc)2 (catalytic amount). The flask is fitted with a reflux condenser and the mixture is heated to 40° C. for 2 hours. The mixture is allowed to cool and was stirred 72 hours. The reaction is quenched with saturated aqueous NaHCO3 and extracted 4× with CH2Cl2. The organic extracts are combined and dried over anhydrous Na2SO4. The mixture is filtered and concentrated in vacuo. The products are isolated by preparative TLC on silica gel to afford the title compound.

후처리

  1. customThe flask is fitted with a reflux condenser
  2. temperatureto cool
  3. customThe reaction is quenched with saturated aqueous NaHCO3
  4. extractionextracted 4× with CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationThe mixture is filtered
  7. concentrationconcentrated in vacuo
  8. customThe products are isolated by preparative TLC on silica gel

출처 및 근거

ORD 기록
ord-f22e648b5aa448089dd965911299c1f7
출처 데이터셋
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05189042

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