118970-36-8

Basic information

• Product Name: (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanenitrile
• Synonyms: (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanenitrile
• CAS NO: 118970-36-8
• Molecular Weight: 356.467
• Mol File: 118970-36-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanenitrile(118970-36-8)
• EPA Substance Registry System: (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanenitrile(118970-36-8)

Safety Data

• Hazardous Substances Data: 118970-36-8(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 5804-85-3 diethylaluminium cyanide 
• 100-39-0 benzyl bromide 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 63-91-2 L-phenylalanine 
• 95437-43-7 (S)-2-(N,N-dibenzylamino)-3-phenylpropanoic acid 

Downstream Products

• 195510-33-9 (2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutanoic acid 
• 170359-24-7 (2R,3S)-1-amino-3-(dibenzylamino)-4-phenylbutan-2-ol 
• 1402829-76-8 C₃₄H₅₀N₂OSi 
• 169331-41-3 (2S,3S)-3-(dibenzylamino)-1-(isobutylamino)-4-phenylbutan-2-ol 
• 1402829-77-9 N-((2S,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide 
• 1402829-78-0 N-((2S,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide 
• 1026449-62-6 (2R,3S)-2-(tert-butyldimethylsilyloxy)-3-(dibenzylamino)-4-phenylbutanenitrile 
• 62023-63-6 (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid 

Relevant articles and documents

Practical synthesis of (2S,3S)-3-amino-2 hydroxy-4-phenylbutyric acid, a key component of HIV protease inhibitors

Synthesis of (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid was achieved by the highly diastereoselective cyanohydrin formation of (S)-2-N,N- dibenzylamino-3-phenylpropanal with acetone cyanohydrin in the presence of trimethyl-aluminum as a key step.

Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: A route to enantiopure β-amino-α-hydroxy acids

Chiral α-dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-β-dibenzylamino-α-hydroxycyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure β-amino-α-hydroxy acids.

STEREOSELECTIVE CYANOHYDRIN-FORMING REACTIONS OF CHIRAL α-AMINO ALDEHYDES

The Lewis acid mediated cyanohydrin-forming addition of Me3SiCN to optically active α-dibenzylamino aldehydes 2 occurs stereoselectively.Chelation controlled adducts 3 result if MgBr2 or TiCl4 is used, whereas the diastereomers 4 are obtained upon employi