1,2,3,5-Tetraacetyl-beta-D-ribofuranose → 2-Amino-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole

HRID 263871

反応式

HRID 263871 の反応式
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1.C(O[C@@H:17]1[O:29][C@H:28]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])(=O)C.[Si](S(C(F)(F)F)(=O)=O)(C)(C)C>C(#N)C>[NH2:1][C:2]1[N:3]([C@@H:17]2[O:29][C@H:28]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]2[O:19][C:20](=[O:22])[CH3:21])[C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1

参加物

5

反応物 3

HCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 4660162-Amino-5,6-dichlorobenzimidazoleHCID 13257444Trifluoromethyl(trimethylsilyl) sulfone

生成物 1

HCID 100498762-Amino-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole収率 15.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

2-Amino-5,6-dichlorobenzimidazole (4) (3 g, 16 mmole) was dissolved in dry acetonitrile (150 ml) and stirred in an inert atmosphere at 60° C. BSA (4.37 ml, 17 mmole) was added and the mixture was stirred for 10 minutes. 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5.09 g, 16 mmole) and TMSTf (3.29 ml, 17 mmole) were added to the clear solution and the mixture was allowed to stir at 60° C. for 1 hr. The mixture was concentrated under reduced pressure and separated on a silica column to yield 1.14 g (15%) of 2-amino-5,6-dichloro-1-(2,3,5,tri-O-acetyl-βribofuranosyl)benzimidazole (43).

後処理

  1. additionBSA (4.37 ml, 17 mmole) was added
  2. stirringthe mixture was stirred for 10 minutes
  3. stirringto stir at 60° C. for 1 hr
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customseparated on a silica column

出典と根拠

ORDレコード
ord-67322e2591fb4d8b827a18c24b8db0c9
出典データセット
uspto-grants-1997_07
特許番号
US05646125

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