Réaction #83102

Équation de réaction

product

1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol

p-toluenesulfonyl chloride

→

desired product

Rendement 57.1%

1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)

Rendement 57.1%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   AutreThe mixture is quenched with water
2. 2
   Extractionextracted with diethyl ether
3. 3
   Lavagewashed with water and saturated sodium chloride
4. 4
   Autredried
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue is purified by chromatography (Silica gel: 50% ethyl acetate/hexane)

Mode opératoire

To a 0° C. solution, under argon, of 0.580 g of product from Example 323 in 10 ml of pyridine is added 0.430 g of p-toluenesulfonyl chloride. The reaction is stirred at room temperature overnight. The mixture is quenched with water, extracted with diethyl ether, washed with water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by chromatography (Silica gel: 50% ethyl acetate/hexane) to give 0.520 g of the desired product.

Source