178201-08-6

Usage

Uses

Used in Research and Scientific Experiments:
(S)-4-Acetyloxy-Mandelonitrile is employed as a research chemical, primarily for its application in scientific experiments. Its unique properties and reactivity make it a valuable compound for exploring various chemical reactions and processes.
Used in Laboratory Settings:
In laboratories, (S)-4-Acetyloxy-Mandelonitrile is used as a specialty chemical, contributing to the advancement of scientific knowledge and understanding of chemical interactions. Its presence in controlled environments allows researchers to study its behavior and potential applications in different fields.
Note: Since the provided materials do not mention specific industries or applications beyond research and laboratory settings, the uses are limited to these contexts. If more information on specific applications in different industries becomes available, the uses can be expanded accordingly.

Upstream product

• 878-00-2 4-formylphenyl acetate 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 74-90-8 hydrogen cyanide 
• 118736-06-4 C₁₃H₁₇NO₃Si 

Downstream Products

• 131100-55-5 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(R)-cyano-((E)-(S)-1-methyl-but-2-enyloxy)-methyl]-phenyl ester 
• 131023-33-1 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(R)-cyano-((E)-(R)-1-methyl-but-2-enyloxy)-methyl]-phenyl ester 
• 133412-38-1 (R)-(4-Hydroxy-phenyl)-((E)-(S)-1-methyl-but-2-enyloxy)-acetonitrile 
• 133412-38-1 (R)-(4-Hydroxy-phenyl)-((E)-(R)-1-methyl-but-2-enyloxy)-acetonitrile 
• 133412-37-0 Acetic acid 4-[(R)-cyano-((E)-(R)-1-methyl-but-2-enyloxy)-methyl]-phenyl ester 
• 133412-37-0 Acetic acid 4-[(R)-cyano-((E)-(S)-1-methyl-but-2-enyloxy)-methyl]-phenyl ester 

Relevant academic research and scientific papers

Cooperative thiourea-Bronsted acid organocatalysis: Enantioselective cyanosilylation of aldehydes with TMSCN

We report a new thiourea - Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enantioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.

Synthesis of the Adrenergic Bronchodilators (R)-Terbutalinel and (R)-Salbutamol from (R)-Cyanohydrins

Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9·HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of (A)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (A)-7b and c to (R)-salbutamol was not yet possible without racemization.

(R)- and (S)-cyanohydrins using oxynitrilases in whole cells

Almond meal and Sorghum bicolor shoots were used as the sources of oxynitrilases for the preparation of a number (R)- and (S)-arylcyanohydrins, respectively, from the corresponding aldehydes in diisopropyl ether. Two different in situ methods were used to introduce hydrogen cyanide into the reaction mixture. In method 1, acetone cyanohydrin decomposes enzymatically and/or chemically to hydrogen cyanide. In method 2, hydrogen cyanide freely evaporates from a solution in diisopropyl ether from one compartment of the reaction vessel and ends up to the other where it dissolves into the reaction mixture.