반응 #2460137

반응 방정식

2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide

4-mercaptobenzonitrile

→

expected product

수율 17.0%

4-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside

수율 17.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   여과the reaction mixture is filtered on Celite® in ethyl acetate
2. 2
   세척The filtrate is washed with a 1N solution of hydrochloric acid, water
3. 3
   건조a 1N solution of sodium hydroxide, water and finally a saturated solution of sodium chloride, dried over magnesium sulfate
4. 4
   기타evaporated under reduced pressure
5. 5
   기타After purification by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v)
6. 6
   기타as the eluent, and precipitation in ether

실험 절차

A suspension of 625 mg (1.76.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 200 mg (1.48.10-3 mol) of 4-mercaptobenzonitrile and a 400 pm molecular sieve in 10 ml of acetonitrile is stirred in the presence of 605 mg (4.4.10-3 mol) of zinc chloride and 310 mg (1.8.10-3 mol) of silver imidazolate, in the absence of light, under an inert atmosphere. After heating at 50° C. for 3 h, the reaction mixture is filtered on Celite® in ethyl acetate. The filtrate is washed with a 1N solution of hydrochloric acid, water, a 1N solution of sodium hydroxide, water and finally a saturated solution of sodium chloride, dried over magnesium sulfate and evaporated under reduced pressure. After purification by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent, and precipitation in ether, 100 mg (yield: 17%) of the expected product are obtained.

출처