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]1([O:74][CH2:75][C:76]([O:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)=[O:77])[CH2:73][CH2:72][CH2:71][CH2:70]1.[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]3([O:74][CH2:75][C:76]([O:78][CH2:79][C:80]4[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=4)=[O:77])[CH2:70][CH2:71][CH2:72][CH2:73]3)[C@@:7]2([CH3:58])[C:5]1=[O:6])(=[O:61])[CH3:62]
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
Reactant: O=C(CO[Si]1(Cl)CCCC1)OCc1ccccc1
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]1(OCC(=O)OCc2ccccc2)CCCC1
Reaction time: 3 h
Yield: 71 %

Procedure:
To a solution of paclitaxel (36 mg; 0.042 mmol) and imidazole (34 mg; 0.505 mmol) in 0.35 mL of dry DMF under nitrogen, was added a crude sample of benzyl 2-((1-chlorosilolan-1-yl)oxy)acetate of undetermined titre. A total of 103 mg of crude silyl chloride was added in 2 portions over a 3 hour period. After another 3 hours at room temperature, the reaction was quenched with H2O and extracted with CH2Cl2 (3×5 mL). The combined organic layers were dried, filtered and concentrated. The residue was purified by column chromatography to give 33 mg (71%) of (2aR,4S,4aS,6R,9S,11S,12S,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4-((1-(2-(benzyloxy)-2-oxoethoxy)silolan-1-yl)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 solid. 1H NMR (300 MHz, CDCl3) δ 8.13-8.10 (m, 2H), 7.77-7.74 (m, 2H), 7.61 (dddd, J=1.5, 1.5, 7.4, 7.4 Hz, 1H), 7.52-7.46 (m, 5H), 7.41-7.32 (m, 10H), 7.16 (d, J=9.0 Hz, 1H), 6.40 (s, 1H), 6.18 (dd, J=8.8, 8.8 Hz, 1H), 5.79 (dd, J=9.0, 2.4 Hz, 1H), 5.68 (d, J=7.0 Hz, 1H), 5.19 (s, 2H), 4.90 (dd, J=9.4, 1.4 Hz, 1H), 4.81-4.77 (m, 1H), 4.57 (dd, J=10.5, 6.7 Hz, 1H), 4.40-4.27 (m, 2H), 4.30 (d, J=8.4 Hz, 1H), 4.18 (d, J=9.1 Hz, 1H), 3.88 (d, J=5.3 Hz, 1H), 3.83 (d, J=6.9 Hz, 1H), 2.62-2.49 (m, 1H), 2.38 (s, 3H), 2.34-2.27 (m, 2H), 2.13 (s, 3H), 1.94 (ddd, J=14.0, 11.0, 2.0 Hz, 1H), 1.84 (s, 3H), 1.69 (s, 3H), 1.62-1.48 (m, 4H), 1.20 (s, 3H), 1.18 (s, 3H), 0.67-0.56 (m, 2H), 0.55-0.42 (m, 2H). MS (ESI+) m/z 1124.5 (M+Na).