반응 #351072

반응 방정식

2,3,5-tri-O-benzyl-D-arabinofuranosyl chloride

Compound 5

2,5,6-Trichlorobenzimidazole

NaH

→

133

수율 95.0%

2,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)benzimidazole

수율 95.0%

용매

CH3CN

CH3CN

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGThe mixture was stirred under N2 for overnight at room temperature
3. 3
   여과The reaction solution was filtered through Celite
4. 4
   기타The filtrate was evaporated
5. 5
   기타to give a syrup
6. 6
   세척eluted with CH2Cl2
7. 7
   workup.ADDITIONThe fractions containing 133
8. 8
   기타evaporated

실험 절차

Compound 5 (598 mg 2.7 mmole) was dissolved in dry CH3CN(60 ml) and 97% NaH (80 mg, 3 mmole) was added. The mixture was stirred under N2 for 1 hour at room temperature. Then 2,3,5-tri-O-benzyl-D-arabinofuranosyl chloride (prepared from 2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose) (1.83 g, 3 mmole)) dissolved in dry CH3CN (20 ml) was added dropwise. The mixture was stirred under N2 for overnight at room temperature. The reaction solution was filtered through Celite. The filtrate was evaporated to give a syrup and this syrup was subjected to flash column chromatography on silica gel (Kieselgel 60, 230-400 mesh) and eluted with CH2Cl2. The fractions containing 133 were combined and evaporated to give 1.6 g (95.0%) of 133. (IR KBr cm-1 : 1140-1060 (C--O--C)).

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