128892-32-0

Basic information

• Product Name: L-Valine, N-methyl-N-[N-methyl-N-[(phenylmethoxy)carbonyl]-L-valyl]-, methyl ester
• CAS NO: 128892-32-0
• Molecular Formula: C21H32N2O5
• Molecular Weight: 392.495
• Mol File: 128892-32-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: L-Valine, N-methyl-N-[N-methyl-N-[(phenylmethoxy)carbonyl]-L-valyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Valine, N-methyl-N-[N-methyl-N-[(phenylmethoxy)carbonyl]-L-valyl]-, methyl ester(128892-32-0)
• EPA Substance Registry System: L-Valine, N-methyl-N-[N-methyl-N-[(phenylmethoxy)carbonyl]-L-valyl]-, methyl ester(128892-32-0)

Safety Data

• Hazardous Substances Data: 128892-32-0(Hazardous Substances Data)

Upstream product

• 42417-65-2 Z-MeVal-OH 
• 3339-44-4 methyl N-methyl-L-valinate hydrochloride 
• 35016-37-6 N-methyl-L-valine methyl ester 
• 13734-41-3 t-Boc-L-valine 
• 53363-91-0 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid methyl ester 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 

Relevant articles and documents

1-Ethyl 2-halopyridinium salts, highly efficient coupling reagents for hindered peptide synthesis both in solution and the solid-phase

1-Ethyl-2-halopyridinium salts, BEP, FEP, BEPH and FEPH, were synthesized and proved to be very effective for the synthesis of hindered peptides containing N-methylated or C(α),C(α)-dialkylated amino acid residues. HPLC monitoring of model reactions indicated that these pyridinium salts demonstrated higher reactivities, lower racemization than the commonly used halogenated uronium and phosphonium salts. The efficiency of these pyridinium type coupling reagents was further proved by the synthesis of a series of hindered oligopeptides and active esters with good yields and convenient workup. The 8-11 tetrapeptide fragment of Cyclosporin A (CsA) and the pentapeptide moiety of Dolastatin 15 were also successfully synthesized using these pyridinium salts. The efficiency of these pyridinium type coupling reagents for SPPS was also demonstrated by the solid-phase synthesis of the extremely hindered 8-11 peptide segment of CsA and the linear undecapeptide of CsO. The mechanism of the pyridinium salt mediated coupling reactions was also studied by 1H NMR, IR and HPLC. It was proposed that the major reactive intermediates were the corresponding acyl halide and acyloxypyridinium salts of the N-protected amino acid or peptide. (C) 2000 Elsevier Science Ltd.

2-Bromo-1-ethyl pyridinium tetrafluoroborate (BEP): A powerful coupling reagent for N-methylated peptide synthesis

2-Bromo-1-ethyl pyridinium tetrafluoroborate (BEP) was firstly utilized to the synthesis of peptides containing N-methyl amino acid residues both in solution and solid phase, and demonstrated high reactivity, low racemization and excellent yields, which w

A novel thiazolium type peptide coupling reagent for hindered amino acids

A highly efficient coupling reagent, 2-bromo-3-ethyl-4-methyl thiazolium tetrafluoroborate (BEMT), was designed, synthesized and successfully applied to the synthesis of oligopeptides containing N-alkyl or α-C-dialkyl amino acids. Its efficiency was evaluated by HPLC and 1H NMR methods, and demonstrated by synthesis of a number of N-methyl-rich peptide segments with good yields and negligible racemization. The mechanism of coupling was studied by HPLC, 1H NMR and IR monitoring; it is proposed that labile (acyloxy)thiazolium salts and N-protected amino acid bromides were the major active intermediates with concomitant formation of N-ethyl-4-methyl thiazolidones and a small amount of oxazolones and N-protected amino acid anhydrides.