173379-58-3

Basic information

• Product Name: (S)-(+)-<2-(4-tert-butylbenzyl)-2-chloromethyl>ethyl acetate
• Synonyms: (S)-(+)-<2-(4-tert-butylbenzyl)-2-chloromethyl>ethyl acetate
• CAS NO: 173379-58-3
• Molecular Weight: 282.81
• Mol File: 173379-58-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-(+)-<2-(4-tert-butylbenzyl)-2-chloromethyl>ethyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-<2-(4-tert-butylbenzyl)-2-chloromethyl>ethyl acetate(173379-58-3)
• EPA Substance Registry System: (S)-(+)-<2-(4-tert-butylbenzyl)-2-chloromethyl>ethyl acetate(173379-58-3)

Safety Data

• Hazardous Substances Data: 173379-58-3(Hazardous Substances Data)

Upstream product

• 173379-57-2 (R)-(+)-<2-(4-tert-butylbenzyl)-2-hydroxymethyl>ethyl acetate 
• 37765-76-7 2-(4-tert-butylbenzyl)diethylmalonate 
• 172477-52-0 2-(4-tert-butylbenzyl)-1,3-propanediol 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 

Downstream Products

• 173379-59-4 (S)-(-)-2-(chloromethyl)-2-(4-tert-butylbenzyl)ethanol 
• 79253-37-5 (S)-3-(4-(tert-butyl)phenyl)-2-methylpropan-1-ol 
• 138320-32-8 (S)-(+)-2-(4-tert-butylbenzyl)-1-chloropropane 
• 76492-90-5 fenpropimorph 

Relevant articles and documents

Enantioselective chemoenzymatic synthesis of the S-enantiomer of the systemic fungicide fenpropimorph

Chemoenzymatic synthesis of the S-(-)-enantiomer of fenpropimorph (S)-1 in high optical and chemical purity is described. One feature of this process entails the enantioselective acetylation of prochiral 1,3-propanediol 4 by Pseudomonas sp. lipases, and subsequent transformation of the monoacetate (R)-5 into the final product by the selected order of transformations that comprise; chlorination or tosylation under non-racemizing conditions, hydrogenolysis of the resulting chloromethyl or tosyl group in (+)-6 and (+)-8, second chlorination of (-)-9, and alkylation of cis-3,5-dimethylmorpholine by 1-chloropropane derivative (+)-10. This sequence of reactions affords (S)-1, the more active enantiomer in the commercialized racemic mixture with systemic fungicidal activity.