107537-99-5

Upstream product

• 2983-06-4 2-acetoxybutanenitrile 
• 129265-90-3 2-(Phenylacetoxy)pentannitril 
• 129265-86-7 2-(Butyryloxy)pentannitril 
• 129313-22-0 (S)-2-(Butyryloxy)pentannitril 
• 74-90-8 hydrogen cyanide 
• 123-72-8 butyraldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 127-08-2 potassium acetate 
• 98-59-9 p-toluenesulfonyl chloride 
• 4111-12-0 (+/-)-2-methyl-2-hydroxyhexanenitrile 
• 773837-37-9 sodium cyanide 
• 129265-91-4 2-(Phenylpropionyloxy)pentannitril 

Relevant academic research and scientific papers

Aliphatic (S)-Cyanohydrins by Enzyme Catalyzed Synthesis

The enzyme catalyzed synthesis of aliphatic (S)-cyanohydrins has been accomplished for the first time by application of a hydroxynitrile lyase from leaves of Hevea brasiliensis.The optical purities of (S)-cyanohydrins obtained are in a range between 60 - 97percent.

High-Throughput Preparation of Optically Active Cyanohydrins Mediated by Lipases

Cyanohydrins are versatile compounds with high applicability in organic synthesis; they are used as starting materials for the synthesis of other chemical targets with high industrial added value. Lipase-mediated kinetic resolution reactions are a promising route for the synthesis of optically active cyanohydrins. These reactions can be carried out through the acylation of cyanohydrins or the deacylation of cyanohydrin esters, with different biocatalysts and under different reaction conditions. Unfortunately, depending on the substrate structure, long reaction times can be required to achieve suitable enantiomeric excesses. In this context, we present a high-throughput protocol for the production of optically active cyanohydrins in continuous-flow mode. The products were obtained with moderate to good enantioselectivity (E values from 8 up to >200) and with productivity values from 2.4 to 8.7 times higher in continuous-flow mode than in batch mode. Moreover, the reaction times were reduced from hours in batch mode to minutes in continuous-flow mode.

A simple separation method for (S)-hydroxynitrile lyase from cassava and its application in asymmetric cyanohydrination

Using an acetone precipitation method, crude (S)-hydroxynitrile lyase [(S)-MeHNL] was separated from Munihot esculenta (cassava) leaves, and used directly as biocatalyst to catalyze asymmetric cyanohydrination and produce cyanohydrins with enantiomeric purities (≥90% ee) significantly greater than those previously reported. The use of a water/i-Pr2O system with an enzyme, NaCN, and appropriate amounts of acetic acid is crucial in improving the stereoselectivity of cyanohydrin formation by minimizing the non-enzymatic reaction and the racemization of the chiral products. The proposed isolation method for crude (S)-MeHNL has a high value because of its simplicity, and low cost as well as the high activity of the crude (S)-MeHNL.

Stereoselective synthesis of β-amino-γ-butyrolactones

A novel synthesis of optically active β-amino-γ-butyrolactones is described. O-Silylated (R)-cyanohydrins (R)-3 (derived from aldehydes 1 by (R)-hydroxynitrile lyase ((R)-PaHNL)-catalyzed addition of HCN) were reacted with allyl Grignard to give amino alc

Approach to (R)- and (S)-ketone cyanohydrins using almond and apple meal as the source of (R)-oxynitrilase

The synthesis of aliphatic and aromatic (R)-ketone cyanohydrins through the addition of hydrogen cyanide to the corresponding ketones and the synthesis of the (S)-enantiomers through the kinetic resolution of racemic ketone cyanohydrins has been studied in the presence of almond or apple meal. Substrate tolerance of the (R)-oxynitrilases towards ketones (R1R2C=O) is highly restricted compared to that of structurally similar aldehydes, reactivity following the order of H>Me>>Et for R2. In the case of aromatic methyl ketones reactivity difference (C6H5>>p-Me-C6H4 for R1) is notable.

Asymmetric synthesis of tetronic acids by Blaise reaction of protected optically active cyanohydrins

An asymmetric synthesis of tetronic acids is described, involving the Blaise reaction of Reformatsky reagents with silyl-protected optically active cyanohydrins, which were prepared by an enzyme-catalysed method.

Enzyme-Catalyzed Reactions, 15. - Preparation of (R)-2-(Sulfonyloxy)nitriles and their Reactions with Acetates - Inversion of the Configuration of Optically Active Cyanohydrins

2-(Sulfonyloxy)nitriles (R)-6,7,8 are obtained in high optical purity from the respective cyanohydrins (R)-2 by sulfonylation with methanesulfonyl chloride (3), toluenesulfonyl chloride (4), and trifluoromethanesulfonic anhydride (5), respectively.In cont

Enzyme-Catalysed Synthesis of Optically Active Aliphatic Cyanohydrins

The enantioselective preparation of aliphatic (R)-cyanohydrins was studied using powdered almond meal, a rich source of mandelonitrile lyase, as a catalyst in organic solvent.The feasibility of powdered almond meal as a catalyst was compared to that of a purified enzyme preparation.

Synthesis of optically active cyanohydrins using almond meal

Asymmetric hydrocyanation of aldehydes was accomplished using almond meal, containing the enzyme oxynitrilase. Optically active cyanohydrins with high levels of enantiomeric purity were obtained following a simple procedure.

Enzyme-Catalyzed Reactions, 7. - Enantioselective Esterification of Racemic Cyanohydrins and Enantioselective Hydrolysis or Transesterification of Cyanohydrin Esters by Lipases

Pure cyanohydrin enantiomers (S)-1/(R)-1 and their O-acyl derivatives (R)-3/(S)-3 are obtained from three different lipase-catalyzed reactions: (i) enantioselective hydrolysis of aliphatic and aromatic racemic cyanohydrin esters 3, ii) enantioselective ac