137271-89-7

Basic information

• Product Name: N-((2-hydroxy-1-naphthyl)methylene)-(S)-valine benzylamide
• Synonyms: N-((2-hydroxy-1-naphthyl)methylene)-(S)-valine benzylamide
• CAS NO: 137271-89-7
• Molecular Weight: 360.456
• Mol File: 137271-89-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-((2-hydroxy-1-naphthyl)methylene)-(S)-valine benzylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-((2-hydroxy-1-naphthyl)methylene)-(S)-valine benzylamide(137271-89-7)
• EPA Substance Registry System: N-((2-hydroxy-1-naphthyl)methylene)-(S)-valine benzylamide(137271-89-7)

Safety Data

• Hazardous Substances Data: 137271-89-7(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 20998-83-8 (S)-benzyl (1-(benzylamino)-3-methyl-1-oxobutan-2-yl)carbamate 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 106566-02-3 L-valine benzylamide 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 

Relevant articles and documents

Peptide-titanium complex as catalyst for asymmetric addition of hydrogen cyanide to aldehyde

The complex of titanium ethoxide and an acyclic dipeptide ester whose terminal amino group is modified to a salicylal-type Schiff base catalyzes the asymmetric addition of hydrogen cyanide to aldehydes with high enantioselectivity. In the reaction of benzaldehyde and hydrogen cyanide, (R)-mandelonitrile is obtained with an enantiomeric excess of 90% when N-((2-hydroxy-1-naphthyl)methylene)-(S)-valyl-(S)-tryptophan methyl ester is employed. In place of the dipeptide, the amide derivatives of an amino acid modified by substituted salicylaldehyde, such as N-(3,5-dibromosalicylidene)-(S)-valine piperidide, exhibit an entirely opposite stereoselectivity to yield S-cyanohydrins with optical purities up to 97% ee. This novel peptide-titanium complex, therefore, enables us to afford optically active cyanohydrins of both absolute configurations by using natural S-amino acids as chiral auxiliaries.