Reaction SMILES: [C:1]([O:9][C@H:10](/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C@@H:11]([N:41]=[N+:42]=[N-:43])[CH2:12][O:13][C@H:14]1[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:17]([OH:18])[C@H:15]1[OH:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:59](Cl)(=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.[CH3:68][OH:69]>N1C=CC=CC=1.C(Cl)Cl>[C:1]([O:9][C@H:10](/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C@@H:11]([NH:41][C:68](=[O:69])[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:10][CH2:11][CH3:12])[CH2:12][O:13][C@H:14]1[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:17]([OH:18])[C@H:15]1[O:16][C:59](=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([O:9][C@H:10](/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C@@H:11]([N:41]=[N+:42]=[N-:43])[CH2:12][O:13][C@H:14]1[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[C@H:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[C@H:17]([O:18][C:68](=[O:69])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:15]1[O:16][C:59](=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
Reactant: CO
Reactant: CCCCCCCCCCCCC/C=C/[C@@H](OC(=O)c1ccccc1)[C@H](CO[C@H]1O[C@H](COCC(=O)OC(C)(C)C)[C@H](OCC(=O)OC(C)(C)C)[C@H](O)[C@H]1O)N=[N+]=[N-]
Reactant: O=C(Cl)c1ccccc1
Solvent: c1ccncc1
Solvent: ClCCl
Product: CCCCCCCCCCCCC/C=C/[C@@H](OC(=O)c1ccccc1)[C@H](CO[C@H]1O[C@H](COCC(=O)OC(C)(C)C)[C@H](OCC(=O)OC(C)(C)C)[C@H](O)[C@H]1OC(=O)c1ccccc1)NC(=O)CCCCCCCCCCCCCCC
Product: CCCCCCCCCCCCC/C=C/[C@@H](OC(=O)c1ccccc1)[C@H](CO[C@H]1O[C@H](COCC(=O)OC(C)(C)C)[C@H](OCC(=O)OC(C)(C)C)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1)N=[N+]=[N-]
Temperature: -15 °C
Reaction time: 0.5 h
Yield: 90 %

Procedure:
A solution of (2S,3R,4E)-3-benzoyloxy-2-azido-1-(4,6-di-O-tert-butyloxycarbonylmethyl-α-D-galactopyranosyloxy)-4-octadecene prepared as described in Example 1-E (0.422 g, 0.51 mmol) in pyridine (12 mL) and methylene chloride (12 mL) was treated with benzoyl chloride (80 μL, 0.69 mmol) at -15° C. The mixture was stirred for 30 minutes at -15° C. then methanol (10 mL) was added and the mixture was stirred for another 18 hours at room temperature. The solvents were evaporated and the residue was co-evaporated with toluene (2×5 mL) and diluted with ethyl acetate (100 mL). This organic phase was washed with 1M aqueous sodium bicarbonate (2×100 mL), water (2×100 mL) and brine (2×100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (60g, 5 to 20% ethyl acetate/hexane) and afforded the title compound (0.420 g, 90%) along with (2S,3R,4E)-3-benzoyloxy-2-azido-1-(2,3-di-O-benzoyl-4,6-di-O-tert-butyloxycarbonylmethyl-α-D-galactopyranosyloxy)-4-octadecene (0.028g).