(2-Chloropyridin-3-yl)boronic acid → 5-(2-Chloro-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside
Reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](Br)[CH:13]=1)(=[O:3])[CH3:2].[Cl:27][C:28]1[C:33](B(O)O)=[CH:32][CH:31]=[CH:30][N:29]=1>>[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:33]2[C:28]([Cl:27])=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:13]=1)(=[O:3])[CH3:2]Participants
3
Procedure
By carrying out the operation analogously to example 1, starting from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained according to preparation IX, and 2-chloro-3-pyridineboronic acid, the desired product is obtained in the form of a white solid (yield=21%).
Workup
- customobtained