반응 #43689

반응 방정식

2,3,4,6-tetra-O-benzyl-1-[7-(4-methylbenzyl)benzo[b]thiophen-2-yl]-D-glucopyranose

triethylsilane

potassium carbonate

→

title compound

수율 80.8%

2-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene

수율 80.8%

용매

acetonitrile

반응 조건

후처리

1. 1
   추출the mixture was extracted with diethyl ether
2. 2
   세척The organic layer washed with water and brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타The solvent was removed under reduced pressure
5. 5
   기타the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1)

실험 절차

To a solution of 2,3,4,6-tetra-O-benzyl-1-[7-(4-methylbenzyl)benzo[b]thiophen-2-yl]-D-glucopyranose (1.2 g) and triethylsilane (0.49 mL), in acetonitrile (15 μL) was added boron trifluoride diethyl ether complex (2.0 mL) at −20° C., and the mixture was stirred for 1 hour. A saturated potassium carbonate aqueous solution was added to the mixture, and the mixture was extracted with diethyl ether. The organic layer washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1) to give the title compound (0.95 g).

출처