Reaction SMILES: [Si:1]([O:8][C@@H:9]([C@@H:35]([CH3:82])/[CH:36]=[CH:37]\[C@@H:38]([O:74][Si:75]([C:78]([CH3:81])([CH3:80])[CH3:79])([CH3:77])[CH3:76])[CH2:39][C@H:40]([O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])[C@H:41]([CH3:65])/[CH:42]=[CH:43]/[CH2:44][O:45][C:46]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C@@H:10]([CH3:34])[CH2:11][CH2:12]/[CH:13]=[CH:14]/[C:15](=[O:33])[C@@H:16]([C@@H:18]1[C@@H:23]([CH3:24])[CH2:22][O:21][CH:20]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[O:19]1)[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CCOC(C)=O.CCCCCC>[Si:1]([O:8][C@@H:9]([C@@H:35]([CH3:82])/[CH:36]=[CH:37]\[C@@H:38]([O:74][Si:75]([C:78]([CH3:81])([CH3:80])[CH3:79])([CH3:77])[CH3:76])[CH2:39][C@H:40]([O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:68])[CH3:69])[C@H:41]([CH3:65])/[CH:42]=[CH:43]/[CH2:44][O:45][C:46]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)[C@@H:10]([CH3:34])[CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:33])[C@@H:16]([C@@H:18]1[C@@H:23]([CH3:24])[CH2:22][O:21][CH:20]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[O:19]1)[CH3:17])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]
Reactant: COc1ccc(C2OC[C@H](C)[C@@H]([C@@H](C)C(=O)/C=C/CC[C@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)/C=C\[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)/C=C/COC(c3ccccc3)(c3ccccc3)c3ccccc3)O[Si](C)(C)C(C)(C)C)O2)cc1
Agent: [BH4-]
Agent: [Na+]
Solvent: CCOC(C)=O
Solvent: CCCCCC
Product: COc1ccc(C2OC[C@H](C)[C@@H]([C@@H](C)C(=O)CCCC[C@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)/C=C\[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)/C=C/COC(c3ccccc3)(c3ccccc3)c3ccccc3)O[Si](C)(C)C(C)(C)C)O2)cc1
Yield: 65417.2 %

Procedure:
The procedure for 40 was used with 69 (1.22 g, 1.04 μmol), NiCl2.6H2O (0.12 g, 0.52 mmol) and NaBH4 (0.079 g, 2.08 mmol) to yield 70 (0.80 g, 65%) after flash column chromatography (EtOAc/hexane 1:9) as a colorless oil: IR (CHCl3) 2956, 2929, 2855, 1713, 1615, 1518, 1461, 1388, 1251, 1077, 1037, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.70-7.66 (m, 6H), 7.57-7.40 (m, 1H), 7.07-7.04 (m, 2H), 5.92-5.77 (m, 2H), 5.65 (m, 1H), 5.64 (s, 1H), 5.52 (m, 1H), 4.78 (m, 1H), 4.30 (dd, J=11.2, 4.6 Hz, 1H), 4.14 (m, 2H), 3.94 (s, 3H), 3.79 (d, J=3.9 Hz, 2H), 3.73 (t, J=11.1 Hz, 1H), 3.61 (m, 1H), 2.92-2.79 (m, 2H), 2.72 (t, J=7.4 Hz, 2H), 2.65 (m, 1H), 2.22 (m, 1H), 1.91-1.71 (m, 4H), 1.65-1.56 (m, 3H), 1.51 (m, 1H), 1.43 (d, J=7.1 Hz, 3H), 1.35 (m, 1H), 1.20 (d, J=6.7 Hz, 3H), 1.14-1.12 (m, 21H), 1.08 (d, J=6.2 Hz, 3H), 1.05-1.03 (m, 9H), 0.96 (d, J=6.7 Hz, 3H), 0.34-0.25 (m, 18H); 13C NMR (75 MHz, CDCl3) 6 211.5, 159.8, 144.4, 144.3, 134.3, 132.9, 132.2, 130.9, 128.6, 127.6, 127.1, 126.8, 113.4, 100.8, 86.7, 83.0, 80.1, 72.8, 72.2, 66.4, 65.0, 55.0, 48.2, 42.3, 41.6, 40.6, 38.0, 35.7, 33.5, 31.2, 27.6, 26.2, 25.91, 25.87, 23.9, 19.4, 18.4, 18.05, 17.99, 14.8, 13.2, 12.0, 9.5, −3.0, −3.6, −3.8, −4.2, −4.3, −4.4; LRMS (ESI) 1197.7 [M+Na]+, 684.2, 541.1; HRMS (ESI) calcd for C71H110O8Si3Na 1197.7406 [M+Na]+, found 1197.7411; [α]20D+4.6 (c 1.1, CHCl3).