220903-34-4

Basic information

• Product Name: (S)-N-tert-butyloxycarbonyl-(3-benzyloxy-2-chloro-4-methoxy)-phenylalanine
• Synonyms: (S)-N-tert-butyloxycarbonyl-(3-benzyloxy-2-chloro-4-methoxy)-phenylalanine
• CAS NO: 220903-34-4
• Molecular Weight: 435.905
• Mol File: 220903-34-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-N-tert-butyloxycarbonyl-(3-benzyloxy-2-chloro-4-methoxy)-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-tert-butyloxycarbonyl-(3-benzyloxy-2-chloro-4-methoxy)-phenylalanine(220903-34-4)
• EPA Substance Registry System: (S)-N-tert-butyloxycarbonyl-(3-benzyloxy-2-chloro-4-methoxy)-phenylalanine(220903-34-4)

Safety Data

• Hazardous Substances Data: 220903-34-4(Hazardous Substances Data)

Upstream product

• 37687-57-3 2-chloro-3-hydroxy-4-methoxybenzaldehyde 
• 1233194-97-2 (S)-N-tert-butoxycarbonyl-(3-benzyloxy-2-chloro-4-methoxy)phenylalanine methyl ester 
• 621-59-0 isovanillin 
• 220903-32-2 (3S,6R)-3-(3-benzyloxy-2-chloro-4-methoxy)benzyl-6-isopropyl-2,5-bisethyl lactim ether 
• 210105-82-1 3-benzyloxy-2-chloro-4-methoxybenzyl bromide 
• 110038-82-9 3-benzyloxy-2-chloro-4-methoxybenzyl alcohol 
• 100-39-0 benzyl bromide 
• 53713-77-2 3-benzyloxy-2-chloro-4-methoxy-benzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 220903-33-3 (S)-N-tert-butyloxycarbonyl-(3-benzyloxy-2-chloro-4-methoxy)-phenylalanine ethyl ester 

Downstream Products

• 778560-53-5 (S)-2-{[(S)-3-(3-Benzyloxy-2-chloro-4-methoxy-phenyl)-2-methylamino-propionyl]-methyl-amino}-3-phenyl-propionic acid allyl ester 
• 220903-37-7 N-tert-butyloxycarbonyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester 
• 210105-92-3 N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine-(R)-(piperazine-2,5-dione)methyl ester 
• 210105-90-1 N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine allyl ester 
• 210105-95-6 N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-(S)-phenylalanyl-N-methyl-(S)-phenylalanine 
• 147317-36-0 pepticinnamin E 
• 210105-85-4 (S)-N-tert-butyloxycarbonyl-N-methyl-(3-benzyloxy-2-chloro-4-methoxy)-phenylalanine 

Relevant articles and documents

Highly stereoselective and efficient synthesis of the dopa analogue in pepticinnamin E via enantioselective hydrogenation of dehydroamino acids

An efficient and new method was developed to prepare the dopa analogue 11 in natural pepticinnamin via catalytic hydrogenation of dehydroamino acids (DDAA) with a good yield and ee. Product 11 is a key intermediate towards the total synthesis of pepticinnamin E and its analogues. TUeBITAK.

Synthesis and in vitro evaluation of the Ras farnesyltransferase inhibitor pepticinnamin E

A modularly built bisubstrate inhibitor, the natural product pepticinnamin E (shown on the right) was synthesized for the first time. In the case of in vitro assays it inhibits the enzyme farnesyltransferase with respect to both the peptide substrate and farnesylpyrophosohate (K1 = 30 and 8 μM, respectively). The inhibitory activity is decisively influenced by the central tripeptide unit and the absolute configuration of the non-proteinogenic amino acid incorporated therein.