Reaction SMILES: [C:1]([O:9][C@@H:10]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:13]([CH2:34][O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:12][C@@H:11]1[O:44][C@@H:45]1[C@@H:50]([CH2:51][O:52][C:53](=[O:60])[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[O:49][C@H:48]([O:61][C@@H:62]2[C@@H:67]([CH2:68][O:69][C:70](=[O:77])[C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[O:66][C@H:65](Br)[C@H:64]([O:79][C:80](=[O:87])[C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=3)[C@H:63]2[O:88][C:89](=[O:96])[C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)[C@H:47]([O:97][C:98](=[O:105])[C:99]2[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=2)[C@H:46]1[O:106][C:107](=[O:114])[C:108]1[CH:113]=[CH:112][CH:111]=[CH:110][CH:109]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:115]([S-:117])#[N:116].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(#N)C>[C:1]([O:9][C@@H:10]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:13]([CH2:34][O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:12][C@@H:11]1[O:44][C@@H:45]1[C@@H:50]([CH2:51][O:52][C:53](=[O:60])[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[O:49][C@H:48]([O:61][C@@H:62]2[C@@H:67]([CH2:68][O:69][C:70](=[O:77])[C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[O:66][C@@H:65]([N:116]=[C:115]=[S:117])[C@H:64]([O:79][C:80](=[O:87])[C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=3)[C@H:63]2[O:88][C:89](=[O:96])[C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)[C@H:47]([O:97][C:98](=[O:105])[C:99]2[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=2)[C@H:46]1[O:106][C:107](=[O:114])[C:108]1[CH:113]=[CH:112][CH:111]=[CH:110][CH:109]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: N#C[S-]
Reactant: O=C(OC[C@H]1O[C@H](Br)[C@H](OC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@@H]1O[C@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@H]2O[C@H](COC(=O)c3ccccc3)[C@@H](OC(=O)c3ccccc3)[C@H](OC(=O)c3ccccc3)[C@H]2OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1)c1ccccc1
Agent: CCCC[N+](CCCC)(CCCC)CCCC
Agent: [I-]
Agent: [K+]
Solvent: CC#N
Product: O=C(OC[C@H]1O[C@@H](N=C=S)[C@H](OC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@@H]1O[C@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@H]2O[C@H](COC(=O)c3ccccc3)[C@@H](OC(=O)c3ccccc3)[C@H](OC(=O)c3ccccc3)[C@H]2OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1)c1ccccc1
Temperature: 75 °C
Reaction time: 8 h
Yield: 64.7 %

Procedure:
Bromide 84 (1.8 g, 1.12 mmol), KSCN (3 equiv., 326 mg), molecular sieves and Bu4NI (cat.) were taken up in dry acetonitrile and stirred at 75° C. overnight. The solvent was evaporated and the residue taken up in DCM and washed with NaHCO3(sat.), before being dried (Na2SO4) and the solvent was evaporated. The crude product was purified using column chromatography (SiO2:Hexane to 35% EtOAc/Hexane, loaded with toluene) to yield 1.15 g of the white solid product (65%). 1H NMR (400 MHz, CDCl3) δ: 8.23-7.12 (m, 50H, Ar), 6.16 (dd, 1H, J3,2=9.6, J3,4=9.6, H-3III), 5.96 (dd, 1H, J3,2=9.6, J3,4=8.2, H-3II), 5.81 (d, 1H, J1,2=4.1, H-1III), 5.75-5.68 (m, 2H, H-3I, H-4III), 5.65 (d, 1H, J1,2=4.1, H-1II), 5.40 (dd, 1H, J2,1=8.2, J2,3=8.2, H-2I), 5.32 (dd, 1H, J2,1=4.1, J2,3=10.2, H-2III), 5.28 (d, 1H, J1,2=8.2, H-1I), 5.13 (dd, 1H, J2,1=4.1, J2,3=10.2, H-2II), 5.00 (dd, 1H, H-6I), 4.77 (dd, 1H, H-6II), 4.72-4.65 (m, 2H, H-6I, H-6II), 4.53-4.41 (m, 5H, H-5II, H-5III, H-4I, H-1II, H-6III), 4.30 (dd, 1H, H-6III), 4.13 (ddd, 1H, H-5I).