27446-39-5

Basic information

• Product Name: L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-a-aspartyl]-, 4-(1,1-dimethylethyl) 1-methyl ester
• CAS NO: 27446-39-5
• Molecular Formula: C26H32N2O7
• Molecular Weight: 484.549
• Mol File: 27446-39-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-a-aspartyl]-, 4-(1,1-dimethylethyl) 1-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-a-aspartyl]-, 4-(1,1-dimethylethyl) 1-methyl ester(27446-39-5)
• EPA Substance Registry System: L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-a-aspartyl]-, 4-(1,1-dimethylethyl) 1-methyl ester(27446-39-5)

Safety Data

• Hazardous Substances Data: 27446-39-5(Hazardous Substances Data)

Upstream product

• 3338-32-7 Z-Asp(OtBu)-OSu 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 33605-72-0 N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester 
• 75-65-0 tert-butyl alcohol 
• 23632-70-4 DCHA salt of the β-tert-butyl ester of N-benzyloxycarbonylaspartic acid 

Downstream Products

• 27446-41-9 methyl ester of N-benzyloxycarbonylglutaminyl-β-O-tert-butylasparaginylphenylalanine 
• 32771-88-3 benzyloxycarbonyl-L-aspartyl-(tert-butyl ester)-L-phenylalanine 
• 33605-72-0 N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester 
• 88621-56-1 Z-Aspt(OtBu)-Phe-OMe 
• 22839-47-0 L-Asp-L-Phe-OMe 
• 88621-57-2 H-Aspt-Phe-Ome 
• 103678-21-3 ZThrTyrThrGlnAsp(OtBu)PheN₂H₃ 
• 103678-20-2 ZThrTyrThrGlnAsp(OtBu)PheOMe 

Relevant articles and documents

Mechanistic insight into the lability of the benzyloxycarbonyl (Z) group in N-protected peptides under mild basic conditions

An unexpected lability of the benzyloxycarbonyl (Z) protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilises the tetrahedral intermediate formed after nucleophilic addition of hydroxide to the carbonyl of the Z group. This effect operates in N-protected tripeptides and tetrapeptides but Z-protected dipeptides are stable under the same conditions due to blockage of the vicinal amide NH by intramolecular H-bonding with the terminal carboxylate moiety. Copyright

SYNTHESIS OF THE HEXAPEPTIDE 11-16 OF THE NATURAL SEQUENCE OF HUMAN CALCITONIN

A new variant of the preparative synthesis of hexapeptide 11-16 of the natural sequence of human calcitonin is described.In several of the stages 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline was used successfully as the condensing agent.The final and in