반응 #1193060

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2,3,4-Tri-O-acetyl-1-thio-β-L-fucopyranose

6-(5-cholesten-3β-yloxy)hexyl iodide

triethylamine

→

title compound

수율 61.0%

6-(5-Cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside

수율 61.0%

용매

dichloromethane

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후처리

1. 1
   기타in 1 day
2. 2
   기타at room temperature
3. 3
   세척The resulting solution is washed with distilled water (20 ml)
4. 4
   건조dried with anhydrous sodium sulfate
5. 5
   농축The filtered solution is concentrated
6. 6
   기타to form a syrup which
7. 7
   세척eluted with chloroform
8. 8
   workup.ADDITIONThe fractions containing the title compound
9. 9
   기타evaporated

실험 절차

2,3,4-Tri-O-acetyl-1-thio-β-L-fucopyranose (10 mmol) is treated with 6-(5-cholesten-3β-yloxy)hexyl iodide (10 mmol) in dichloromethane (30 ml) containing triethylamine (10 mmol). The reaction takes place in 1 day at room temperature under nitrogen. The resulting solution is washed with distilled water (20 ml) and dried with anhydrous sodium sulfate. The filtered solution is concentrated to form a syrup which is put on a silica gel column and eluted with chloroform followed by 1.0% ethanol in chloroform. The fractions containing the title compound, as determined by thin layer chromatography, are pooled and evaporated to give the title compound in 61% yield [α]D -4° (c 1.5, chloroform).

출처