تفاعل #43689

معادلة التفاعل

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

triethylsilane

potassium carbonate

→

title compound

المردود 80.8%

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

المردود 80.8%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر