Reaction #83102

Reaction equation

product

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

p-toluenesulfonyl chloride

→

desired product

Yield 57.1%

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

Yield 57.1%

Solvents

pyridine

Conditions

Workup

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

Procedure

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