Reaction SMILES: [CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].N1C=CN=C1.Cl[Si:69]([CH3:85])([CH3:84])[CH2:70][CH2:71][CH2:72][CH2:73][C:74]([O:76][CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)=[O:75].[SiH3]Cl>CN(C=O)C>[C:60]([O:59][C@@H:4]1[C:3]2[C:15]([CH3:16])([CH3:17])[C@@:14]([OH:41])([CH2:18][C@H:19]([O:20][C:21](=[O:22])[C@H:23]([OH:40])[C@@H:24]([NH:31][C:32](=[O:33])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:2]=2[CH3:1])[C@@H:13]([O:42][C:43](=[O:44])[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:12]2[C@:11]3([O:53][C:54](=[O:55])[CH3:56])[CH2:51][O:52][C@@H:10]3[CH2:9][C@H:8]([O:57][Si:69]([CH2:70][CH2:71][CH2:72][CH2:73][C:74]([O:76][CH2:77][C:78]3[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=3)=[O:75])([CH3:85])[CH3:84])[C@@:7]2([CH3:58])[C:5]1=[O:6])(=[O:61])[CH3:62]
Reactant: C[Si](C)(Cl)CCCCC(=O)OCc1ccccc1
Reactant: CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O
Agent: [SiH3]Cl
Agent: c1c[nH]cn1
Solvent: CN(C)C=O
Product: CC(=O)O[C@H]1C(=O)[C@@]2(C)C([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O[Si](C)(C)CCCCC(=O)OCc1ccccc1
Reaction time: 12 h
Yield: 27 %

Procedure:
To a solution of Paclitaxel (52.5 mg; 0.061 mmol) and imidazole (40.1 mg; 0.590 mmol) in 0.25 mL of dry DMF under nitrogen was added the crude benzyl 5-(chlorodimethylsilyl)pentanoate of undetermined titre. A total of 197 mg of crude silyl chloride was added in 4 portions along with an additional 12 mg portion of imidazole over a 29 hour period. After stirring for an additional 12 hours, the reaction mixture was concentrated under reduced pressure and the resulting crude material was purified by column chromatography (silica gel, 0-50% ethyl acetate in hexanes, 40 minute gradient) to give 33 mg (27%) of (2aR,4S,4aS,6R,9S,11S,12S,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4-(((5-(benzyloxy)-5-oxopentyl)dimethylsilyl)oxy)-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetate as a white waxy solid. 1H NMR (500 MHz, CDCl3) δ 8.14-8.10 (m, 2H), 7.77-7.74 (m, 2H), 7.61 (dddd, J=1.3, 1.3, 7.4, 7.4 Hz, 1H), 7.52-7.46 (m, 5H), 7.43-7.38 (m, 4H), 7.36-7.29 (m, 6H), 7.07 (d, J=8.9 Hz, 1H), 6.38 (s, 1H), 6.17 (dd, J=9.6, 8.4 Hz, 1H), 5.80 (dd, J=9.0, 2.4 Hz, 1H), 5.67 (d, J=7.0 Hz, 1H), 5.11 (s, 2H), 4.90 (d, J=9.4 Hz, 1H), 4.79 (s, 1H), 4.37 (dd, J=10.3, 6.9 Hz, 1H), 4.29 (d, J=8.4 Hz, 1H), 4.18 (d, J=8.4 Hz, 1H), 3.80 (d, J=6.9 Hz, 1H) 3.63 (s, 1H), 2.45 (ddd, J=14.4, 9.5, 6.8 Hz, 1H), 2.37 (s, 3H), 2.37-2.33 (m, 2H), 2.31 (dd, J=8.8, 5.4 Hz, 1H), 2.16 (s, 3H), 1.88-1.81 (m, 3H), 1.68 (s, 3H), 1.66-1.61 (m, 3H), 1.34-1.27 (m, 2H), 1.21 (s, 3H), 1.18 (s, 3H), 0.92-0.82 (m, 2H), 0.60-0.48 (m, 2H), 0.08 (s, 3H), 0.07 (s, 3H). MS (ESI+) m/z 1102.4 (M+1); HPLC 96% (AUC), tR 22.72 min (Method A).