Reaction #6090

Reaction equation

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

4-mercaptobenzonitrile

→

expected product

Yield 64.0%

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

Yield 64.0%

Solvents

toluene

acetonitrile

Conditions

Workup

1. 1
   FiltrationAfter the reaction medium has been filtered on Celite® in ethyl acetate
2. 2
   Otherthe organic phase obtained
3. 3
   Washis washed with a 1N solution of HCl twice
4. 4
   Dryinga 1N solution of sodium hydroxide and finally water, dried over magnesium sulfate
5. 5
   Otherevaporated under reduced pressure
6. 6
   OtherAfter precipitation in ether

Procedure

A suspension of 16.9 g (47.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 6 g (43.10-3 mol) of 4-mercaptobenzonitrile and 3.5 g (43.10-3 mol) of zinc oxide (ZnO) in 120 ml of anhydrous toluene and 120 ml of acetonitrile is stirred under an inert atmosphere, in the presence of a molecular sieve (1 mm), for 18 hours, at 50° C. After the reaction medium has been filtered on Celite® in ethyl acetate, the organic phase obtained is washed with a 1N solution of HCl twice, a 1N solution of sodium hydroxide and finally water, dried over magnesium sulfate and evaporated under reduced pressure. After precipitation in ether, 11.30 g (yield: 64%) of the expected product are obtained.

Source