1,2,3,5-Tetraacetyl-beta-D-ribofuranose → 1-(4-nitrobenzyl)-4-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)oxy-1H-imidazole-5-carboxamide
Reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][CH:6]1Cl)(=[O:3])[CH3:2].C(O[C@@H]1O[C@H](COC(=O)C)[C@@H](OC(=O)C)[C@H]1OC(=O)C)(=O)C.[C:42]([C:45]1[N+:49]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][CH:52]=2)=[CH:48][NH:47][C:46]=1[O-:60])(=[O:44])[NH2:43]>>[N+:57]([C:54]1[CH:53]=[CH:52][C:51]([CH2:50][N:49]2[C:45]([C:42]([NH2:43])=[O:44])=[C:46]([O:60][C@@H:6]3[O:7][C@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:5]3[O:4][C:1](=[O:3])[CH3:2])[N:47]=[CH:48]2)=[CH:56][CH:55]=1)([O-:59])=[O:58]Participants
4
Procedure
Following a procedure similar to that of Example 1 but using 2,3,5-tri-O-acetyl-D-ribofuranosyl chloride prepared from 2.50 g of 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose and 1.022 g of 5-carbamoyl-1-(4-nitrobenzyl)imidazolium-4-olate there was obtained 0.986 g of 1-(4-nitrobenzyl)-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)oxy-1H-imidazole-5-carboxamide which was recrystallized from ethanol. m.p. 155.5°-156.5° C.
Sources & evidence
- ORD record
- ord-cbd40d06246e48ea8072d2832bd45149
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04464531
Reaction notes
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