102036-16-8

Basic information

• Product Name: (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate
• Synonyms: (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate
• CAS NO: 102036-16-8
• Molecular Weight: 306.767
• Mol File: 102036-16-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate(102036-16-8)
• EPA Substance Registry System: (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate(102036-16-8)

Safety Data

• Hazardous Substances Data: 102036-16-8(Hazardous Substances Data)

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 102129-99-7 (R,S)-2-hydroxy-3-chloropropyl p-toluenesulfonate 
• 108-24-7 acetic anhydride 

Downstream Products

• 102130-01-8 (R)-2-acetoxy-3-chloropropyl p-toluenesulfonate 
• 83398-53-2 (R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate 
• 127062-61-7 Acetic acid (S)-1-chloromethyl-2-(toluene-4-sulfonyloxy)-ethyl ester 
• 67800-61-7 (S)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate) 

Relevant articles and documents

Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine

The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates.