Acetobromo-alpha-D-glucuronic acid methyl ester → methyl 1-O-[5-carbamoyl-1-(4-nitrobenzyl)imidazole-4-yl]-2,3,4-tri-O-acetyl-beta-D-glucopyranuronate
Reaction equation
[C:1]([C:4]1[N+:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:7][NH:6][C:5]=1[O-:19])(=[O:3])[NH2:2].Br[C@H:21]1[O:38][C@H:37]([C:39]([O:41][CH3:42])=[O:40])[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]1[O:23][C:24](=[O:26])[CH3:25]>>[C:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)[CH:7]=[N:6][C:5]=1[O:19][C@@H:21]1[O:38][C@H:37]([C:39]([O:41][CH3:42])=[O:40])[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]1[O:23][C:24](=[O:26])[CH3:25])(=[O:3])[NH2:2]Participants
3
Procedure
Following a procedure similar to that of Example 1 but using 1.442 g of 5-carbamoyl-1-(4-nitrobenzyl)imidazolium-4-olate and 4.37 g of methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucopyranuronate there was obtained methyl 1-O-[5-carbamoyl-1-(4-nitrobenzyl)imidazole-4-yl]-2,3,4-tri-O-acetyl-β-D-glucopyranuronate. The resulting product as such was used as the starting compound in the following Example 19.
Sources & evidence
- ORD record
- ord-7f2f449530db4ca78ead8a76f23163cb
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04464531
Reaction notes
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