Reaction SMILES: C(O)(=O)C.[CH2:5]([O:8][C:9]([O:11][C@H:12]1[C@H:25]([O:26][P:27]2(=[O:38])[O:33][CH2:32][C:31]3[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=3[CH2:29][O:28]2)[C@@H:24]([CH2:39][O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:23][C@@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C@@H:13]1[N:48]=[N+]=[N-])=[O:10])[CH:6]=[CH2:7].[C:51](Cl)([O:53][CH2:54][CH:55]1[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:61]2[C:56]1=[CH:57][CH:58]=[CH:59][CH:60]=2)=[O:52].CCN(C(C)C)C(C)C>C(Cl)Cl.C(OCC)(=O)C.[Zn].CCCCCC.C(OCC)(=O)C>[CH2:5]([O:8][C:9]([O:11][C@H:12]1[C@H:25]([O:26][P:27]2(=[O:38])[O:33][CH2:32][C:31]3[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=3[CH2:29][O:28]2)[C@@H:24]([CH2:39][O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:23][C@@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C@@H:13]1[NH:48][C:51]([O:53][CH2:54][CH:55]1[C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][C:61]=2[C:62]2[C:67]1=[CH:66][CH:65]=[CH:64][CH:63]=2)=[O:52])=[O:10])[CH:6]=[CH2:7]
Reactant: C=CCOC(=O)O[C@@H]1[C@@H](N=[N+]=[N-])[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](COCc2ccccc2)[C@H]1OP1(=O)OCc2ccccc2CO1
Reactant: O=C(Cl)OCC1c2ccccc2-c2ccccc21
Agent: [Zn]
Solvent: CCOC(C)=O
Solvent: CC(=O)O
Solvent: ClCCl
Product: C=CCOC(=O)O[C@@H]1[C@@H](NC(=O)OCC2c3ccccc3-c3ccccc32)[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](COCc2ccccc2)[C@H]1OP1(=O)OCc2ccccc2CO1
Temperature: 25 °C
Reaction time: 2 h
Yield: 79.9 %

Procedure:
Acetic acid (300 μL, 5.20 mmol) was added dropwise to a stirred suspension of 10 (1.40 g, 2.08 mmol) and zinc powder (676 mg, 10.4 mmol) in DCM (15 mL). The reaction mixture was stirred at room temperature for 2 h, after which it was diluted with ethyl acetate (50 mL). The solids were removed by filtration and washed with ethyl acetate (2×10 mL). The combined filtrates were washed with saturated aqueous NaHCO3 (2×40 mL) and brine (2×40 mL). The organic phase was dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to afford a crude amine as a pale yellow oil. Rf=0.21 (hexane/ethyl acetate, 1/1, v/v). FmocCl (645 mg, 2.50 mmol) was added to a stirred solution of the crude amine and DIPEA (435 μL, 2.50 mmol) in DCM (15 mL) at 0° C. The reaction mixture was stirred at room temperature for 5 h, after which it was diluted with DCM (40 mL) and washed with brine (2×50 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, 4/1-2/1, v/v) to afford 11 as a colorless solid (1.45 g, 80% over two steps). Rf=0.54 (hexane/ethyl acetate, 1/1, v/v). [α]25D=−3.9° (c=1.0, CDCl3); 1H NMR (500 MHz, CDCl3): δ 7.78-7.20 (m, 17H, aromatic), 5.92-5.82 (m, 1H, OCH2CH═CH2), 5.42 (broad, 1H, H-3), 5.31 (d, 1H, J=17.6 Hz, OCH2CH═CH2), 5.20-5.07 (m, 6H, H-1, OCH2CH═CH2, C6H4(CH2O)P), 4.67-4.56 (m, 5H, H-4, OCH2CH═CH2, CH2Ph), 4.41-4.23 (m, 3H, COOCH2, Fmoc, COOCH2CH, Fmoc), 3.89-3.87 (broad, 1H, H-6a), 3.76-3.74 (broad, 2H, H-5, H-6b), 3.49-3.47 (m, 1H, H-2), 0.88 (s, 4H, SiC(CH3)3), 0.14 (s, 3H, Si(CH3)2), 0.10 (s, 3H, Si(CH3)2). 13C NMR (75 MHz, CDCl3): δ 155.52 (C═O), 154.80 (C═O), 143.71-119.94 (aromatic), 131.34 (OCH2CH═CH2), 118.85 (OCH2CH═CH2), 95.41 (C-1), 74.77 (C-4), 73.85 (C-5), 73.47 (CH2Ph), 68.94, 68.57, 68.50, 68.42 (C-3, C-6, OCH2CH═CH2, OC6H4(CH2O)P), 68.50 (OC6H4(CH2O)P), 67.12 (CO2CH2CH, Fmoc), 58.69 (C-2), 47.04 (CO2CH2CH, Fmoc), 25.52 (SiC(CH3)3), 17.88 (SiC(CH3)3), −4.26 (Si(CH3)2), −5.38 (Si(CH3)2). HR MS (m/z) calculated for C46H54NO12PSi[M+Na]+, 894.3051. found, 894.3937.