Reaction #6089

Reaction equation

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

4-mercaptobenzonitrile

→

expected product

Yield 23.0%

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

Yield 23.0%

Solvents

acetonitrile

Conditions

Workup

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

Procedure

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