Reaction SMILES: S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[CH2:16]([O:54][CH:55]1[C@H:59]2[C@H:60]([O:80][Si:81]([C:84]([CH3:87])([CH3:86])[CH3:85])([CH3:83])[CH3:82])[N:61]([C:72]([O:74][CH2:75][C:76]([Cl:79])([Cl:78])[Cl:77])=[O:73])[C:62]3[CH:69]=[CH:68][C:67]([O:70][CH3:71])=[CH:66][C:63]=3[C:64](=[O:65])[N:58]2[CH2:57][C:56]1=O)[CH2:17][CH2:18][O:19][CH:20]1[C@H:24]2[C@H:25]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[N:26]([C:37]([O:39][CH2:40][C:41]([Cl:44])([Cl:43])[Cl:42])=[O:38])[C:27]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:28]=3[C:29](=[O:30])[N:23]2[CH2:22][C:21]1=[O:53].N1C=CC=CC=1>CCOC(C)=O.CCCCCC>[CH2:16]([O:54][CH:55]1[C@H:59]2[C@H:60]([O:80][Si:81]([C:84]([CH3:87])([CH3:86])[CH3:85])([CH3:83])[CH3:82])[N:61]([C:72]([O:74][CH2:75][C:76]([Cl:79])([Cl:78])[Cl:77])=[O:73])[C:62]3[CH:69]=[CH:68][C:67]([O:70][CH3:71])=[CH:66][C:63]=3[C:64](=[O:65])[N:58]2[CH:57]=[C:56]1[O:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])[CH2:17][CH2:18][O:19][CH:20]1[C@H:24]2[C@H:25]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[N:26]([C:37]([O:39][CH2:40][C:41]([Cl:44])([Cl:43])[Cl:42])=[O:38])[C:27]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:28]=3[C:29](=[O:30])[N:23]2[CH:22]=[C:21]1[O:53][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:10])=[O:8]
Reactant: O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F
Reactant: COc1ccc2c(c1)C(=O)N1CC(=O)C(OCCCOC3C(=O)CN4C(=O)c5cc(OC)ccc5N(C(=O)OCC(Cl)(Cl)Cl)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]34)[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)N2C(=O)OCC(Cl)(Cl)Cl
Solvent: CCOC(C)=O
Solvent: c1ccncc1
Solvent: CCCCCC
Product: COc1ccc2c(c1)C(=O)N1C=C(OS(=O)(=O)C(F)(F)F)C(OCCCOC3C(OS(=O)(=O)C(F)(F)F)=CN4C(=O)c5cc(OC)ccc5N(C(=O)OCC(Cl)(Cl)Cl)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]34)[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)N2C(=O)OCC(Cl)(Cl)Cl
Yield: 0.1 %

Procedure:
Anhydrous triflic anhydride (3.09 mL, 5.19 g, 18.4 mmol, 22 eq) taken from a freshly opened ampule was added rapidly in one portion to a vigorously stirred solution of ketone 12 (0.98 g, 0.84 mmol) and anhydrous pyridine (1.49 mL, 1.46 g, 18.4 mmol, 22 eq) in dry DAM (50 mL) at room temperature under a nitrogen atmosphere. The initial precipitate dissolved gradually and the solution eventually turned a dark red colour. The reaction mixture was allowed to stir for 4.5 h when TLC (80:20 v/v EtOAc/hexane) revealed the complete consumption of the starting material. The mixture was poured into cold saturated NaHCO3 (60 mL) and extracted with DCM (3×80 mL). The combined organic layers were then washed with saturated CuSO4 (2×125 mL), brine (125 mL) and dried (MgSO4). Filtration and evaporation of the solvent afforded the crude product which was purified by flash column chromatography (80:20 v/v hexane/EtOAc) to afford triflate 13 as a light yellow glass (0.74 mg, 61%): [α]25 D=+46.0° (c=0.33, CHCl3); 1H NMR (400 MHz, CDCl3) δ 7.23 (s, 2H, H6), 7.19 (s, 2H, H3), 6.77 (s, 2H, H9), 5.94 (d, 2H, J=8.9 Hz, H11), 5.23 (d, 2H, J=12.0 Hz, Troc CH2), 4.31-4.28 (m, 2H, OCH2CH2CH2O), 4.18 (d, 2H, J=12.2 Hz, Troc CH2), 4.15-4.13 (m, 2H, OCH2CH2CH2O), 3.95-3.91 (m, 8H, OCH3×2, H11a), 3.35 (dd, 2H, J=11.0, 16.6 Hz, H1), 2.84 (d, 2H, J=16.6 Hz, H1), 2.46-2.44 (m, 2H, OCH2CH2CH2O), 0.89 (s, 18H, TBS CH3×6), 0.29 and 0.26 (s×2, 12H, TBS CH3×4); 13C NMR (100.6 MHz, CDCl3) δ 164.9 (Cquat), 153.6 (Cquat), 151.0 (Cquat), 149.5 (Cquat), 136.0 (Cquat), 127.7 (Cquat), 123.9 (Cquat), 121.0 (C3), 114.0 (C9), 110.9 (C6), 95.1 (Troc CCl3), 86.3 (C11), 74.8 (Troc CH2), 65.0 (OCH2CH2CH2O), 60.6 (C11a), 56.2 (OCH3), 34.4 (C1), 28.8 (OCH2CH2CH2O), 25.6 (TBS CH3), 17.8 (TBS Cquat); IR (CHCl3) 3020, 2957, 2860, 1725, 1674, 1651, 1604, 1516, 1466, 1454, 1431, 1409, 1329, 1312, 1274, 1216, 1138, 1113, 1083, 1042, 1006, 900, 840, 757, 668, 646, 610 cm−1; MS (ES), m/z (relative intensity) 1461 ([M+21]+., 100), 1440 (M+., 55).