反応 #43689

反応方程式

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

triethylsilane

potassium carbonate

→

title compound

収率 80.8%

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

収率 80.8%

溶媒

acetonitrile

反応条件

後処理

1. 1
   抽出the mixture was extracted with diethyl ether
2. 2
   洗浄The organic layer washed with water and brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他The solvent was removed under reduced pressure
5. 5
   その他the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1)

実験手順

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).

出典