134983-50-9

Upstream product

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

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 
• 131023-34-2 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(R)-cyano-((S)-1-methyl-butoxy)-methyl]-phenyl ester 
• 131023-34-2 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(R)-cyano-((R)-1-methyl-butoxy)-methyl]-phenyl ester 
• 133412-39-2 Acetic acid 4-[(R)-cyano-((S)-1-methyl-butoxy)-methyl]-phenyl ester 
• 133412-39-2 Acetic acid 4-[(R)-cyano-((R)-1-methyl-butoxy)-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 
• 133412-41-6 (R)-(4-Hydroxy-phenyl)-((S)-1-methyl-butoxy)-acetonitrile 
• 133412-41-6 (R)-(4-Hydroxy-phenyl)-((R)-1-methyl-butoxy)-acetonitrile 
• 131023-32-0 4'-Octyloxy-biphenyl-4-carboxylic acid 4-((R)-allyloxy-cyano-methyl)-phenyl ester 
• 134983-52-1 (R)-Allyloxy-(4-hydroxy-phenyl)-acetonitrile 
• 134983-51-0 Acetic acid 4-((R)-allyloxy-cyano-methyl)-phenyl ester 
• 133412-37-0 Acetic acid 4-[(R)-cyano-((E)-(R)-1-methyl-but-2-enyloxy)-methyl]-phenyl ester 

Relevant academic research and scientific papers

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.