67321-63-5

Basic information

• Product Name: (R)-N-benzyl-β³-homophenylglycine
• Synonyms: (R)-N-benzyl-β³-homophenylglycine
• CAS NO: 67321-63-5
• Molecular Weight: 255.316
• Mol File: 67321-63-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-N-benzyl-β³-homophenylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-benzyl-β³-homophenylglycine(67321-63-5)
• EPA Substance Registry System: (R)-N-benzyl-β³-homophenylglycine(67321-63-5)

Safety Data

• Hazardous Substances Data: 67321-63-5(Hazardous Substances Data)

Upstream product

• 150931-58-1 rac-methyl 3-(benzylamino)-3-phenylpropanoate 
• 5678-50-2 β-phenyl β-(benzylamino) propionic acid 
• 14990-09-1 tert-butyl cinnamate 
• 309757-64-0 (3R,αS)-tert-Butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-phenyl propanoate 
• 160460-40-2 [(S)-1-(4-Methoxy-phenyl)-ethyl]-[1-phenyl-meth-(E)-ylidene]-amine 
• 120343-46-6 (S)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine 
• 100-52-7 benzaldehyde 

Downstream Products

• 19340-71-7 (R)-1-benzyl-4-phenylazetidin-2-one 

Relevant articles and documents

Mechanochemical enzymatic resolution of N-benzylated-β3-amino esters

The use of mechanochemistry to carry out enantioselective reactions has been explored in the last ten years with excellent results. Several chiral organocatalysts and even enzymes have proved to be resistant to milling conditions, which allows for rather efficient enantioselective transformations under ball-milling conditions. The present article reports the first example of a liquid-assisted grinding (LAG) mechanochemical enzymatic resolution of racemic β3-amino esters employing Candida antarctica lipase B (CALB) to afford highly valuable enantioenriched N-benzylated-β3-amino acids in good yields. Furthermore the present protocol is readily scalable.

Orthogonal N,N-deprotection strategies of β-amino esters

β-Amino esters derived from the stereoselective conjugate addition of homochiral lithium N-benzyl-N-α-methyl-4-methoxybenzylamide to α,β-unsaturated esters may be orthogonally mono-N-deprotected under either oxidative or acid-promoted reaction conditions. Further oxidative deprotection affordsβ-amino acids or β-lactams.