Reaction SMILES: [C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:9]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:8]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:7][C@H:6]1[O:36][C@@H:37]1[C@@H:66]([CH2:67][O:68][CH2:69][C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[O:65][C@H:40]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][N:47]([CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:48]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:49])[C@H:39]([N:76]=[N+:77]=[N-:78])[C@H:38]1[OH:79])(=[O:3])[CH3:2].[CH3:80][O:81][C@@H:82]1[C@@H:91]([O:92][CH2:93][C:94]2[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=2)[C@@H:90]([OH:100])[C@@H:89]([CH3:101])[O:88][C@@H:83]1OCC=C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C1(C)C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:9]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@@H:8]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:7][C@H:6]1[O:36][C@@H:37]1[C@@H:66]([CH2:67][O:68][CH2:69][C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)[O:65][C@H:40]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][N:47]([CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:48]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:49])[C@H:39]([N:76]=[N+:77]=[N-:78])[C@H:38]1[O:79][C@H:83]1[O:88][C@H:89]([CH2:101][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:90]([O:100][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:91]([O:92][CH2:93][C:94]2[CH:95]=[CH:96][CH:97]=[CH:98][CH:99]=2)[C@H:82]1[O:81][CH2:80][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:3])[CH3:2]
Reactant: C=CCO[C@H]1O[C@H](C)[C@H](O)[C@H](OCc2ccccc2)[C@H]1OC
Reactant: CC(=O)O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](N=[N+]=[N-])[C@@H](OCCCCCN(Cc3ccccc3)C(=O)OCc3ccccc3)O[C@@H]2COCc2ccccc2)O[C@H](COCc2ccccc2)[C@H](OCc2ccccc2)[C@@H]1OCc1ccccc1
Agent: C[Si](C)(C)OS(=O)(=O)C(F)(F)F
Solvent: Cc1ccccc1
Product: CC(=O)O[C@H]1[C@H](O[C@H]2[C@H](O[C@H]3O[C@H](COCc4ccccc4)[C@H](OCc4ccccc4)[C@H](OCc4ccccc4)[C@H]3OCc3ccccc3)[C@@H](N=[N+]=[N-])[C@@H](OCCCCCN(Cc3ccccc3)C(=O)OCc3ccccc3)O[C@@H]2COCc2ccccc2)O[C@H](COCc2ccccc2)[C@H](OCc2ccccc2)[C@@H]1OCc1ccccc1
Temperature: -50 °C
Reaction time: 0.5 h
Yield: 115.9 %

Procedure:
A mixture of 6 (0.098 g, 0.14 mmol) and 7 (0.1 g, 0.092 mmol) was co-evaporated with dry toluene (3×7 mL) and dried in vacuo for 4 h. The dried compounds were dissolved in a mixture of diethyl ether and dichloromethane (7 mL, 5/1, v/v) and 4 Å MS (0.28 g) was added. The mixture was stirred under an atmosphere of argon for 30 min and then cooled (−50° C.). TMSOTf (2.5 μL, 0.014 mmol) was added and the reaction mixture was allowed to reach 0° C. gradually over a period of 1 h. The reaction was then quenched by the addition of pyridine (20 μL), diluted with dichloromethane (7 mL), and filtered through celite. The filtrate was washed with aqueous NaHCO3 (sat., 7 mL) and the organic layer was dried (MgSO4) and filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate, 4/1, v/v) to give 8 (0.13 g, 86%) as a clear oil. Rf=0.35 (hexane/ethyl acetate, 4/1, v/v). [α]25D=+59.4 (c 1.72, CHCl3); 1H (500 MHz, CDCl3): δ 7.35-7.14 (m, 50H, aromatic), 5.76 (d, 1H, J1,2=3.0 Hz, H-1″), 5.28 (t, 1H, J2,3=9.5 Hz, J1,2=8.0 Hz, H-2′), 5.18-5.16 (bd, 2H, CH2-LCbz), 4.89-4.84 (m, 2H, CHH, OBn, H-1), 4.80-4.71 (dd, 3H, 3×CHH, OBn), 4.68-4.62 (m, 5H, 3×CHH, OBn, H-1′), 4.54-4.39 (m, 8H, 3×CH2, OBn, CH2-LBn), 4.35-4.24 (m, 3H, CHH, OBn, H-3, H-5″), 4.18-4.04 (m, 5H, CH2, OBn, H-4, H-3″, H-2″), 3.99 (bs, 1H, H-4″), 3.84 (bs, 1H, H-4′), 3.80-3.74 (m, 2H, H-6a, H-5), 3.65-3.51 (m, 4H, H-6b, H-6′a, H-6″a,b), 3.44-3.30 (m, 5H, CH2-L, H-2, H-5′, H-6′), 3.23-3.17 (m, 3H, CH2-L, H-3′), 1.90 (s, 3H, COCH3), 1.51-1.46 (m, 4H, 2×CH2-L), 1.26-1.20 (m, 2H, CH2-L). 13C (75 MHz, CDCl3): δ 169.26, 139.36, 139.18, 138.70, 138.28, 138.24, 138.15, 138.12, 137.08, 128.77, 128.68, 128.63, 128.59, 128.48, 128.42, 128.37, 128.36, 128.34, 128.29, 128.05, 127.95, 127.93, 127.82, 127.80, 127.70, 127.60, 127.53, 127.41, 127.35, 127.30, 99.64 (C-1′), 97.63 (C-1), 96.22 (C-1″), 81.04, 78.64, 76.84, 76.51, 76.28, 75.54, 74.92, 74.68, 73.68, 73.58, 73.45, 73.23, 72.51, 72.40, 72.19, 71.96, 70.49, 70.16, 69.17, 68.76, 68.33, 68.22, 67.37, 62.64, 53.66, 29.13, 23.41, 21.26. HR-MALDI-TOF/MS (m/z) calcd for C96H104N4O18[M+Na]+: 1623.7246. found: 1623.7242.