HCID 87736159, compound → HCID 87736993, compound

HRID 2252503Notes

Reaction equation

HRID 2252503 reaction equation
[CH3:1][O:2][C:3]1[CH:91]=[CH:90][C:6]([CH2:7][O:8][C@@H:9]([C@@H:84]([CH3:89])/[CH:85]=[CH:86]\[CH:87]=[CH2:88])[C@@H:10]([CH3:83])[C@H:11]([O:75][Si:76]([C:79]([CH3:82])([CH3:81])[CH3:80])([CH3:78])[CH3:77])[CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([CH3:74])[C@@H:17]([O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])[C@@H:18]([CH3:65])/[CH:19]=[CH:20]\[C@@H:21]([O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])[CH2:22][C@H:23]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[C@H:24]([CH3:48])/[CH:25]=[CH:26]/[CH2:27][O:28]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1>CCOC(C)=O.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C@@H:9]([C@@H:84]([CH3:89])/[CH:85]=[CH:86]\[CH:87]=[CH2:88])[C@@H:10]([CH3:83])[C@H:11]([O:75][Si:76]([C:79]([CH3:82])([CH3:81])[CH3:80])([CH3:77])[CH3:78])[CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([CH3:74])[C@@H:17]([O:66][Si:67]([C:70]([CH3:71])([CH3:72])[CH3:73])([CH3:69])[CH3:68])[C@@H:18]([CH3:65])/[CH:19]=[CH:20]\[C@@H:21]([O:57][Si:58]([C:61]([CH3:62])([CH3:63])[CH3:64])([CH3:60])[CH3:59])[CH2:22][C@H:23]([O:49][Si:50]([C:53]([CH3:54])([CH3:55])[CH3:56])([CH3:52])[CH3:51])[C@H:24]([CH3:48])/[CH:25]=[CH:26]/[CH2:27][OH:28])=[CH:90][CH:91]=1

Participants

3

Reactant 1

HCID 87736159HCID 87736159, compound

Product 1

HCID 87736993HCID 87736993, compoundYield 177,769.797%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The procedure for 45 was used with 74 (0.58 g, 0.22 μmol), ZnBr (0.25 g, 1.11 mmol) to yield 75 (0.42 g, 89%) after flash column chromatography (EtOAc/hexane 3:17) as a colorless oil: IR (CHCl3) 3402, 2956, 2929, 2856, 1614, 1514, 1471, 1251, 1085, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.47-7.44 (m, 2H), 7.04-7.01 (m, 2H), 6.76 (ddd, J=16.8, 10.6, 10.5 Hz, 1H), 6.19 (t, J=11.0 Hz, 1H), 5.87-5.72 (m, 3H), 5.59 (t, J=10.0 Hz, 1H), 5.45 (dd, J=10.9, 8.3 Hz, 1H), 5.35 (d, J=16.8 Hz, 1H), 5.27 (d, J=10.2 Hz, 1H), 4.75-4.65 (m, 3H), 4.22 (d, J=4.5 Hz, 2H), 4.09 (m, 1H), 3.94 (s, 3H), 3.83 (m, 1H), 3.56 (m, 1H), 3.51 (m, 1H), 3.17 (m, 1H), 2.77 (m, 1H), 2.57 (m, 1H), 1.95 (m, 1H), 1.85 (m, 1H), 1.78-1.55 (m, 8H), 1.53-1.40 (m, 3H), 1.29 (d, J=6.7 Hz, 3H), 1.56-1.06 (m, 45H), 1.01 (d, J=6.7 Hz, 3H), 0.29-0.22 (m, 24H); 13C NMR (75 MHz, CDCl3) δ 158.9, 134.8, 134.5, 132.8, 132.4, 132.3, 131.2, 129.2, 129.1, 128.9, 117.1, 113.6, 84.3, 80.2, 75.0, 72.4, 72.2, 66.5, 63.6, 55.1, 42.3, 41.5, 40.5, 37.9, 35.7, 35.2, 33.8, 28.1, 26.2, 25.9, 25.6, 19.3, 18.8, 18.4, 18.2, 18.0, 14.6, 13.0, 9.2, −3.0, −3.5, −3.7, −3.9, −4.3, −4.4, −4.5; LRMS (ESI) 1095.7 [M+Na]+, 809.6, 677.5, 537.4, 413.2; HRMS (ESI) calcd for C61H116O7Si4Na 1095.7696 [M+Na]+, found 1095.7712; [α]20D+4.8 (c 1.7, CHCl3).

Sources & evidence

ORD record
ord-c275122a783049b9afba67391ad79faf
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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