122269-89-0

Basic information

• Product Name: L-Alanine, (2S)-2-phenyl-N-[(phenylmethoxy)carbonyl]glycyl-, methyl ester
• CAS NO: 122269-89-0
• Molecular Formula: C20H22N2O5
• Molecular Weight: 370.405
• Mol File: 122269-89-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-Alanine, (2S)-2-phenyl-N-[(phenylmethoxy)carbonyl]glycyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, (2S)-2-phenyl-N-[(phenylmethoxy)carbonyl]glycyl-, methyl ester(122269-89-0)
• EPA Substance Registry System: L-Alanine, (2S)-2-phenyl-N-[(phenylmethoxy)carbonyl]glycyl-, methyl ester(122269-89-0)

Safety Data

• Hazardous Substances Data: 122269-89-0(Hazardous Substances Data)

Upstream product

• 5491-18-9 Z-Phg 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 133010-29-4 Z-Phg-F 
• 5491-18-9 Z-D-Phg 
• 133010-29-4 Z-D-Phg-F 
• 5491-18-9 (S)-N-(benzyloxycarbonyl)phenylglycine 

Relevant articles and documents

β-Lactams derived from phenylalanine and homologues: effects of the distance between the aromatic rings and the α-stereogenic reactive center on the memory of chirality

The enantioselectivity in the base-promoted cyclization of N-chloroacetyl derivatives of Phe, Phg, and Hph is dependent on the side-chain length, with the best results for Phg analogues (up to 74% ee). In contrast, shortening of the N-substituent, from a

Investigation of the Reaction between Amino Acids or Amino Acid Esters and 9-Formylfluorene and Its Equivalents. Possible Utility of the Derived Enamines as Amino Group Protectants

Treatment of 9-(hydroxymethylene)fluorene/9-formylfluorene (storable as the hemiacetal with methanol, 7) with amino acids and amino acid esters yields the corresponding enamines 8, which may be considered to be hydrocarbon analogues of N-formyl amino acid derivatives.Attempted coupling of the free acids 8 (R'=H) with amino acid esters failed, suggesting insufficient reduction in basicity of the amino group due to the enamine residue.The introduction of electron-withdrawing substituents into the fluorene ring decreases the basicity sufficiently to allow normal peptide coupling reactions, as for example with the 2,7-dichloro analogues derived from 17.Thus phenylalanine derivative 18 treated with leucine methyl ester and DCC gave dipeptide 19.The DC-FM-bar group could be removed by catalytic transfer hydrogenolysis.Mild acid hydrolysis represents a second general deblocking technique for the FM-bar function.It was demonstrated in a model study involving the highly sensitive amino acid α-phenylglycine that the FM-bar protecting group was less prone to cause racemization than the benzyloxycarbonyl function.It was demonstrated that the simple pentapeptide leucine enkephalin 29 could be synthesized using α-DC-FM-bar protection along with tert-butyl-based side chain protecting groups.