1,2-Dichloroethane → benzyl 6-{bis[2-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}-6-oxohexanoate
Reaction equation
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([N:16]([CH2:21][C:22]([OH:24])=O)[CH2:17][C:18]([OH:20])=O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]([CH2:37][CH2:38][NH2:39])[C@@H:27]1[O:35][C@@H:34]([CH3:36])[C@@H:32]([OH:33])[C@@H:30]([OH:31])[C@@H:28]1[OH:29].[CH2:40](Cl)[CH2:41]Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C@@H:27]1([O:26][CH2:37][CH2:38][NH:39][C:22](=[O:24])[CH2:21][N:16]([CH2:17][C:18](=[O:20])[NH:39][CH2:38][CH2:37][O:26][C@@H:27]2[O:35][C@@H:40]([CH3:41])[C@@H:32]([OH:33])[C@@H:30]([OH:31])[C@@H:28]2[OH:29])[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:25])[O:35][C@@H:34]([CH3:36])[C@@H:32]([OH:33])[C@@H:30]([OH:31])[C@@H:28]1[OH:29]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 2,2′-{[6-(benzyloxy)-6-oxohexanoyl]imino}diacetic acid (800 mg, 2.277 mmol) in DMF (12 mL) at room temperature was added 2-aminoethyl α-L-fucopyranoside (1.132 g, 5.46 mmol), DMAP (834 mg, 6.83 mmol) and EDC (1.528 g, 7.97 mmol). After stirring at rt for 16 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on C18 reverse phase silica gel (120 g), eluting with 0-40% AcCN in water, to give the title compound. LC-MS Method A: m/e=730.26 [M+1]; Rt=1.42 min.
Workup
- concentrationthe reaction mixture was concentrated
- customthe residue was purified by flash chromatography on C18 reverse phase silica gel (120 g)
- washeluting with 0-40% AcCN in water
Sources & evidence
- ORD record
- ord-3ff88908113a4ee9aed8e25a586426fb
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09427475B2
Reaction notes
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