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:75][CH2:76][C:77]([O:79][CH2:80][C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)=[O:78])[CH2:74][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]([O:40][Si:69]3([O:75][CH2:76][C:77]([O:79][CH2:80][C:81]4[CH:82]=[CH:83][CH:84]=[CH:85][CH:86]=4)=[O:78])[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]3)[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]([OH:57])[C@@:7]2([CH3:58])[C:5]1=[O:6])(=[O:61])[CH3:62]
Reactant: O=C(CO[Si]1(Cl)CCCCC1)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[Si]4(OCC(=O)OCc5ccccc5)CCCCC4)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O
Yield: 66 %

Procedure:
To a solution of paclitaxel (38 mg; 0.044 mmol) and imidazole (38 mg; 0.0556 mMol) in 0.3 mL of dry DMF under nitrogen, was added a crude sample of benzyl 2-((1-chlorosilinan-1-yl)oxy)acetate of undetermined titre. A total of 135 mg of crude silyl chloride was added in 3 portions over a 21 hour period. After stirring for another hour, the reaction was concentrated under reduced pressure and the residue was directly purified via column chromatography to give 32.8 mg of (2aR,4S,4aS,6R,9S,11S,12S,12bS)-9-(((2R,3S)-3-benzamido-2-((1-(2-(benzyloxy)-2-oxoethoxy)silinan-1-yl)oxy)-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-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 (66%) as a colorless glassy solid. 1H NMR (500 MHz, CDCl3) δ 8.13-8.12 (m, 2H), 7.78-7.77 (m, 2H), 7.61 (dddd, J=1.4, 1.4, 7.4, 7.4 Hz, 1H), 7.53-7.50 (m, 2H), 7.46 (dddd, J=1.4, 1.4, 7.4, 7.4 Hz, 1H), 7.41-7.31 (m, 12H), 7.28-7.24 (m, 1H), 6.27 (s, 1H), 6.24 (dd, J=9.4, 9.4 Hz, 2H), 5.75 (dd, J=8.7, 3.6 Hz, 1H), 5.67 (d, J=7.2 Hz, 1H), 5.18-5.09 (m, 2H), 5.04 (d, J=3.6 Hz, 1H), 4.96 (dd, J=9.7, 2.0 Hz, 1H), 4.43 (ddd, J=10.8, 6.5, 4.2 Hz, 1H), 4.30 (d, J=8.4 Hz, 1H), 4.20 (d, J=8.5 Hz, 1H), 4.20-4.11 (m, 2H), 3.80 (d, J=6.9 Hz, 1H), 2.54 (ddd, J=14.8, 9.6, 6.4 Hz, 1H), 2.48 (s, 3H), 2.31 (dd, J=15.3, 9.5 Hz, 1H), 2.22 (s, 3H), 2.03 (dd, J=15.7, 8.8 Hz, 1H) 1.91-1.82 (m, 4H), 1.68 (s, 3H), 1.65-1.52 (m, 4H), 1.37-1.27 (m, 2H), 1.23 (s, 3H), 1.12 (s, 3H), 0.72-0.67 (m, 1H), 0.65-0.58 (m, 2H), 0.48 (ddd, J=14.6, 9.1, 5.2 Hz, 1H). MS (ESI+) m/z 1138.4 (M+Na); HPLC 80% (AUC), tR 22.11 min (Method A).