Tri-O-acetyl-5-deoxy-D-ribofuranose → 5-Nitro-1-(2,3-di-o-acetyl-5-deoxy-beta-d-ribofuranosyl)-n-(1-methylethyl)-1h-benzimidazol-2-amine

HRID 2227191Notes

Reaction equation

HRID 2227191 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]2[NH:8][C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].C(O[CH:21]1[O:33][C@H:32]([CH3:34])[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]1[O:23][C:24](=[O:26])[CH3:25])(=O)C>>[N+:1]([C:4]1[CH:16]=[CH:15][C:7]2[N:8]([C@@H:21]3[O:33][C@H:32]([CH3:34])[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]3[O:23][C:24](=[O:26])[CH3:25])[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 11196237Tri-O-acetyl-5-deoxy-D-ribofuranoseHCID 178456831HCID 178456831, compound

Product 1

HCID 572643085-Nitro-1-(2,3-di-o-acetyl-5-deoxy-beta-d-ribofuranosyl)-n-(1-methylethyl)-1h-benzimidazol-2-amine

Procedure

5-nitro-N-(1-methylethyl)-1H-benzimidazol-2-amine (1.1 g) was coupled to 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose according to General Procedure II. The crude product was purified by flash chromatography (1:1 ethyl acetate/hexanes) to yield the title compound (0.420 g) as a mixture of 5,6 regioisomers. MS (AP): m/z 443 (M+Na).

Workup

  1. customThe crude product was purified by flash chromatography (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4636d1a22478473882403a2a920e163c
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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