Reacción #6127

Ecuación de reacción

trichloroacetonitrile

NaH

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

→

expected product

Rendimiento 53.0%

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

Rendimiento 53.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe reaction medium is filtered on silica in methylene chloride
2. 2
   Otropurified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent

Procedimiento

1.5 ml (15.10-3 mol) of trichloroacetonitrile and 70 mg of NaH (2.3.10-3 mol of NaH in 80% dispersion) are added to a solution of 1 g (3.42.10-3 mol) of 2, 3, 4 -tri-O-acetyl-5-thio-α-D-xylopyranose in 10 ml of methylene chloride. After 4 h at room temperature, the reaction medium is filtered on silica in methylene chloride and then purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent. 790 mg (yield: 53%) of the expected product are obtained after crystallization from an ethyl acetate/hexane mixture.

Fuente