Réaction #6089

Équation de réaction

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

4-mercaptobenzonitrile

→

expected product

Rendement 23.0%

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

Rendement 23.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction mixture is then filtered on Celite® in ethyl acetate
2. 2
   Lavagesubsequently washed with a 1N solution of sodium hydroxide, water
3. 3
   Séchagefinally a saturated solution of sodium chloride, dried over magnesium sulfate
4. 4
   Autreevaporated under reduced pressure
5. 5
   AutreAfter precipitation in ether

Mode opératoire

A suspension of 192 mg (0.44.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate, 71 mg (0.52.10-3 mol) of 4-mercaptobenzonitrile, 20 mg (0.15.10-3 mol) of zinc chloride and a 400 pm sieve in 2 ml of acetonitrile is stirred for 4 h under an inert atmosphere. The reaction mixture is then filtered on Celite® in ethyl acetate and subsequently washed with 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 precipitation in ether, 42 mg (yield: 23%) of the expected product are obtained.

Source