Reaction SMILES: [Si:1]([O:18][CH2:19][CH2:20][C@H:21]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)[CH2:22][C@H:23]1[O:28][C@@H:27]([CH2:29][C@@H:30]([O:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:26][C@@H:25]([OH:42])[CH2:24]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:53][Si:54](Cl)([CH3:56])[CH3:55].CCN(CC)CC>C(Cl)Cl>[Si:1]([O:18][CH2:19][CH2:20][C@H:21]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)[CH2:22][C@H:23]1[O:28][C@@H:27]([CH2:29][C@@H:30]([O:37][Si:38]([CH3:39])([CH3:41])[CH3:40])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:26][C@@H:25]([O:42][Si:54]([CH3:56])([CH3:55])[CH3:53])[CH2:24]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: C[Si](C)(C)Cl
Reactant: CCOC(=O)C[C@@H](C[C@H]1C[C@@H](O)C[C@@H](C[C@H](CCO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)OCc2ccc(OC)cc2)O1)O[Si](C)(C)C
Solvent: ClCCl
Solvent: CCN(CC)CC
Product: CCOC(=O)C[C@@H](C[C@H]1C[C@@H](O[Si](C)(C)C)C[C@@H](C[C@H](CCO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)OCc2ccc(OC)cc2)O1)O[Si](C)(C)C
Reaction time: 12 h
Yield: 95.9 %

Procedure:
To a solution of alcohol 4 (83.1 mg, 0.111 mmol, 1.0 equiv) in CH2Cl2 (11 mL, 0.01 M) in a 25 mL rb flask was added TMSCl (60.3 mg, 0.555 mmol, 5.0 equiv) and NEt3 (112.3 mg, 1.11 mmol, 10.0 equiv) dropwise via syringe. After 12 h at rt, the reaction was quenched by the addition of water (5.0 mL). The phases were separated and the aqueous phase was extracted with Et2O (3×10 mL). The organic phases were combined, dried over Na2SO4 and concentrated under reduced pressure. Purification was accomplished by flash chromatography on a 3.5×13 cm column, eluting with 10% EtOAc/hexanes, collecting 18 mm×150 mm test tube fractions. The product containing fractions (5-9) were combined and concentrated under reduced pressure to give the product 18 (87.6 mg, 96% yield) as colorless oil: Rf=0.52 (20% EtOAc/Hexanes); [α]D20=+12.5 (c=2.71, CHCl3); 500 MHz 1H NMR (CDCl3) δ 7.69 (ddd, J=4.4, 1.4, 1.4 Hz, 2H), 7.67 (dd, J=4.0, 1.7 Hz, 2H), 7.45-7.35 (m, 6H), 7.18 (d, J=8.7 Hz, 2H), 6.85 (d, J=8.7 Hz, 2H), 4.45 (d, J=11.1 Hz, 1H), 4.37 (d, J=11.1 Hz, 1H), 4.37-4.30 (m, 1H), 4.14-4.02 (m, 2H), 3.90-3.84 (m, 1H), 3.80 (s, 3H), 3.80-3.71 (m, 3H), 3.56-3.50 (m, 1H), 3.45-3.38 (m, 1H), 2.50 (d, J=4.7 Hz, 1H), 2.48 (d, J=2.7 Hz, 1H), 1.86-1.72 (m, 5H), 1.66-1.54 (m, 3H), 1.20 (t, J=7.1 Hz, 3H), 1.05 (s, 9H), 0.13 (s, 9H), 0.11 (s, 9H); 125 MHz 13C NMR (CDCl3) δ 171.8, 159.3, 135.8, 135.8, 134.1, 134.1, 129.8, 129.6, 127.9, 114.0, 72.9, 72.2, 72.1, 71.8, 68.8, 66.8, 60.7, 60.5, 55.5, 44.0, 43.1, 42.3, 42.3, 41.9, 37.7, 27.1, 19.4, 14.4, 0.5, 0.5; 125 MHz DEPT 13C NMR (CDCl3) CH3 δ 55.5, 27.1, 14.4, 0.5, 0.5; CH2 δ 71.8, 60.7, 60.5, 44.0, 43.1, 42.3, 42.3, 41.9, 37.7; CH δ 135.8, 129.8, 129.6, 127.9, 114.0, 72.9, 72.2, 72.1, 68.8, 66.8; C δ 171.8, 159.3, 135.8, 134.1, 134.1, 19.4; IR (neat) 3071, 2952, 2859, 1613, 1588, 1467, 1428, 1377, 1302, 1250, 1175, 1110, 744 cm−1; HRMS (ESI/APCI) calcd for C45H70O8NaSi3 (M+Na) 845.4271. found 845.4263.