121232-85-7

Upstream product

• 110270-49-0 (R)-3-acetoxy-2-benzyl-1-propanol 
• 49769-78-0 2-benzyl-malonic acid dimethyl ester 
• 2612-30-8 2-benzyl-1,3-propanediol 
• 90107-01-0 rac-2-hydroxymethyl-3-phenyl-propyl acetate 

Downstream Products

• 116111-79-6 (R)-3-(acetylthio)-2-benzylpropanoic acid 
• 124815-67-4 (S)-2-acetylthiomethyl-3-phenylpropanoic acid 
• 81110-73-8 N-(S-2-acetylthiomethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester 
• 81110-73-8 (R)-benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate 
• 147383-72-0 (S)-2-hydroxymethyl-3-phenylpropionic acid 

Relevant academic research and scientific papers

New asymmetric synthesis of dexecadotril and ecadotril starting from a single precursor

We describe herein a method providing access to both enantiomers of 3-acetylthio-2-benzylpropionic acid via enzymatic desymmetrization of 2-benzyl-1,3-propanediol. These compounds are respectively the starting materials for the synthesis of ecadotril, and dexecadotril, which are powerful inhibitors of NEP (EC 3.4.24.11) and have been developed as therapeutic agents.

PROCESS FOR THE ASYMMETRIC SYNTHESIS OF S-ACYL DERIVATIVES OF 2-MERCAPTOMETHYL -3- PHENYL PROPANOIC ACID, APPLICATION TO THE SYNTHESIS OF N-(MERCAPTOACYL) AMINO ACID DERIVATIVES

Process for the asymmetric synthesis of S-acyl derivatives of 2-mercaptomethyl-3-phenylpropanoic acid of formula (I): characterized in that it comprises the steps consisting in:a) preparing the diol (VI) by reduction of a malonic ester (V) in the presence of a hydride; b) preparing the monoacetates (VII R) or (VII S) respectively; c) subjecting these monoacetates to an oxidation in order to form the acids (IX S) or (IX R);d) saponifying the compounds (IX S) or (IX R) in order to form the hydroxy acids (X S) or (X R);e) thioacylating the hydroxy acids (X S) or (X R) with a mercapto acid R. sub.1 SH (XI), according to a Mitsunobu-type reaction, in order to lead to the desired acids (I R) (I S) respectively and application to the synthesis of N-(mercaptoacyl)amino acid derivatives (II). STR1

Preparative Bioorganic Chemistry, XI. - Preparation of the Enantiomers of Paraconic Acid Employing Lipase-Mediated Asymmetric Hydrolysis of Prochiral Diacetates as the Key Step

(S)-(-)-Paraconic acid (1) was prepared from 2-(acetoxymethyl)-3-phenylpropyl acetate (4) by its asymmetric hydrolysis with pig pancreatic lipase as the key step.Similarly, (R)-(+)-1 was prepared from 2-(acetoxymethyl)-4-pentenyl acetate (2) by its asymme