Reaktionsgleichung
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4](=[O:12])[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH:16][CH:17]1[O:33][C@H:32]([CH2:34][OH:35])[C@@H:22]([O:23][CH2:24][C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)[C@H:20]([OH:21])[C@@H:18]1[OH:19].CN(C=O)C.ON1C2C=CC=CC=2N=N1.[NH:51]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][C:53](O)=[O:54].C(N=C=NCCCN(C)C)C>>[NH:51]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][C:53]([NH:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4](=[O:12])[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:54].[OH:16][CH:17]1[O:33][C@H:32]([CH2:34][OH:35])[C@@H:22]([O:23][CH2:24][C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)[C@H:20]([OH:21])[C@@H:18]1[OH:19]Komponenten
6
Versuchsvorschrift
To a cold solution of Asp(O-cHex)-Man(4-MBzl) (46.7 g, 86.4 mmol) in DMF (100 mL) diisopropylethylamine (15 mL, 86.1 mmol) was added. N-Hydroxybezotriazole (14.0 g, 104 mmol) was added followed by Boc-Gly (16.6 g, 94.8 mmol). The reaction mixture was stirred in the cold for a few minutes, and N-ethyl-N'(dimethylaminopropyl)carbodiimide (18.2 g, 94.9 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The reaction mixture was concentrated to a small volume and poured into 1.5 L of aqueous 10% K2CO3. The precipitated product was collected by filtration and was washed with water to a neutral pH to afford the titled compound (50.6 g).
Aufarbeitung
- stirringstirred for 18 h
- concentrationThe reaction mixture was concentrated to a small volume
- additionpoured into 1.5 L of aqueous 10% K2CO3
- filtrationThe precipitated product was collected by filtration
- washwas washed with water to a neutral pH
Quellen und Nachweise
- ORD-Eintrag
- ord-bcef87ed7a7043ef86ee001ff10769ae
- Quelldatensatz
- uspto-grants-1998_03
- Patentnummer
- US05726192
Verknüpfte Notizen
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