Reaction SMILES: N1C=CC=CC=1.[CH2:7]([O:14][CH2:15][C@H:16]1[O:21][C@@H:20]([O:22][CH2:23][C@H:24]2[O:37][C@@H:28]([O:29][Si](C(C)(C)C)(C)C)[C@H:27]([NH:38][C:39](=[O:61])[CH2:40][C@H:41]([O:53][CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C@@H:26]([O:62][C:63](=[O:85])[CH2:64][C@H:65]([O:77][CH2:78][C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH3:76])[C@@H:25]2[O:86][CH2:87][C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)[C@H:19]([NH:94][C:95](=[O:123])[CH2:96][C@H:97]([O:109][C:110](=[O:122])[CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH3:121])[CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH2:105][CH2:106][CH2:107][CH3:108])[C@@H:18]([O:124][C:125](=[O:155])[CH2:126][C@H:127]([O:139][C:140](=[O:154])[CH2:141][CH2:142][CH2:143][CH2:144][CH2:145][CH2:146][CH2:147][CH2:148][CH2:149][CH2:150][CH2:151][CH2:152][CH3:153])[CH2:128][CH2:129][CH2:130][CH2:131][CH2:132][CH2:133][CH2:134][CH2:135][CH2:136][CH2:137][CH3:138])[C@@H:17]1[O:156][P:157]1(=[O:168])[O:163][CH2:162][C:161]2[CH:164]=[CH:165][CH:166]=[CH:167][C:160]=2[CH2:159][O:158]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1.C(OCC)(=O)C>[CH2:7]([O:14][CH2:15][C@H:16]1[O:21][C@@H:20]([O:22][CH2:23][C@H:24]2[O:37][C@H:28]([OH:29])[C@H:27]([NH:38][C:39](=[O:61])[CH2:40][C@H:41]([O:53][CH2:54][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C@@H:26]([O:62][C:63](=[O:85])[CH2:64][C@H:65]([O:77][CH2:78][C:79]3[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=3)[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH3:76])[C@@H:25]2[O:86][CH2:87][C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)[C@H:19]([NH:94][C:95](=[O:123])[CH2:96][C@H:97]([O:109][C:110](=[O:122])[CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH3:121])[CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH2:105][CH2:106][CH2:107][CH3:108])[C@@H:18]([O:124][C:125](=[O:155])[CH2:126][C@H:127]([O:139][C:140](=[O:154])[CH2:141][CH2:142][CH2:143][CH2:144][CH2:145][CH2:146][CH2:147][CH2:148][CH2:149][CH2:150][CH2:151][CH2:152][CH3:153])[CH2:128][CH2:129][CH2:130][CH2:131][CH2:132][CH2:133][CH2:134][CH2:135][CH2:136][CH2:137][CH3:138])[C@@H:17]1[O:156][P:157]1(=[O:168])[O:158][CH2:159][C:160]2[CH:167]=[CH:166][CH:165]=[CH:164][C:161]=2[CH2:162][O:163]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
Reactant: CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@H](OC[C@H]2O[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OCc3ccccc3)[C@@H](OC(=O)C[C@@H](CCCCCCCCCCC)OCc3ccccc3)[C@@H]2OCc2ccccc2)O[C@H](COCc2ccccc2)[C@H]1OP1(=O)OCc2ccccc2CO1
Solvent: c1ccncc1
Solvent: C1CCOC1
Solvent: CCOC(C)=O
Product: CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@H](OC[C@H]2O[C@H](O)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OCc3ccccc3)[C@@H](OC(=O)C[C@@H](CCCCCCCCCCC)OCc3ccccc3)[C@@H]2OCc2ccccc2)O[C@H](COCc2ccccc2)[C@H]1OP1(=O)OCc2ccccc2CO1
Temperature: 25 °C
Reaction time: 5 h
Yield: 84.3 %

Procedure:
HF/pyridine (50 μL) was added dropwise to a stirred solution of 30 (20.0 mg, 0.0087 mmol) in THF (3 mL). The reaction mixture was stirred at room temperature for 5 h, after which it was diluted with ethyl acetate (15 mL), and washed with saturated aqueous NaHCO3 (2×25 mL) and brine (2×20 mL). The organic phase was dried (MgSO4) and filtered. Next, the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate, 3/1-4/3, v/v) to give 32 as a white solid (16.0 mg, 84%). Rf=0.38 (hexane/ethyl acetate, 1/1, v/v). 1H NMR (500 MHz, CDCl3): δ 7.39-7.19 (m, 24H, aromatic), 6.36 (d, 1H, JNH′,2′=7.0 Hz, NH′), 6.28 (d, 1H, JNH,2=9.5 Hz, NH), 5.52 (d, 1H, J1′2′=9.0 Hz, H-1′), 5.51 (t, 1H, J2′,3′=J3′,4′=9.5 Hz, H-3′), 5.41 (t, 1H, J2,3=J3,4=10.0 Hz, H-3), 5.27-5.25 (m, 1H, H-3L), 5.15-4.96 (m, 6H, H-1, H-3L, C6H4(CH2O)2P), 4.64-4.43 (m, 9H, H-4′, 4×CH2Ph), 4.23-4.19 (m, 1H, H-2), 4.13-4.09 (m, 1H, H-5), 3.94-3.82 (m, 4H, H-6a, H-6′a, 2×H-3S), 3.76-3.69 (m, 3H, H-5′, H-6′a, H-6b), 3.36-3.33 (m, 2H, H-2′, H-4), 2.69-2.27 (m, 12H, 2×H-2L, 2×H-2S, 2×H-2L′), 1.58 (broad, 12H, 2×H-4L, 2×H-4S, 2×H-3L′), 1.26 (broad, 108H, 54×CH2, lipid), 0.91-0.81 (m, 18H, 6×CH3, lipid). HR MS (m/z) calculated for C130H2O2N2O22PSi[M+Na]+, 2202.4776. found, 2202.8279.