3350-41-2

Basic information

• Product Name: L-Phenylalanine, 2-methyl-N-[(phenylmethoxy)carbonyl]alanyl-, methyl ester
• CAS NO: 3350-41-2
• Molecular Formula: C22H26N2O5
• Molecular Weight: 398.459
• Mol File: 3350-41-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, 2-methyl-N-[(phenylmethoxy)carbonyl]alanyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, 2-methyl-N-[(phenylmethoxy)carbonyl]alanyl-, methyl ester(3350-41-2)
• EPA Substance Registry System: L-Phenylalanine, 2-methyl-N-[(phenylmethoxy)carbonyl]alanyl-, methyl ester(3350-41-2)

Safety Data

• Hazardous Substances Data: 3350-41-2(Hazardous Substances Data)

Upstream product

• 15030-75-8 Z-Aib-ONp 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 15030-72-5 Z-Aib-OH 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 

Downstream Products

• 7625-54-9 α-Benzyloxycarbonyl-amino-isobutyryl-L-phenylalanin-hydrazid 
• 3350-43-4 (2S)-2-[(2-[[(benzyloxy)carbonyl]amino]-2-methylpropanoyl)amino]-3-phenylpropanoic acid 
• 3350-44-5 [1-((S)-4-benzyl-5-oxo-4,5-dihydro-oxazol-2-yl)-1-methyl-ethyl]-carbamic acid benzyl ester 
• 15204-58-7 Benzyloxycarbonyl-aminoisobutyryl-L-Phe-L-Phe-methylester 
• 15204-59-8 Benzyloxycarbonyl-aminoisobutyryl-L-Phe-D-Phe-methylester 
• 15204-55-4 Benzyloxycarbonyl-aminoisobutyryl-L-Phe-D-phenylglycin-methylester 
• 15204-54-3 Benzyloxycarbonyl-aminoisobutyryl-L-Phe-L-phenylglycin-methylester 
• 15204-56-5 Benzyloxycarbonyl-aminoisobutyryl-L-Phe-L-Ala-methylester 
• 15204-57-6 Benzyloxycarbonyl-aminoisobutyryl-L-Phe-D-Ala-methylester 
• 15204-60-1 Benzyloxycarbonyl-amino-isobutyryl-L-Phe-α-aminoisobuttersaeure-methylester 
• 107169-39-1 Cbz-D-Pro-Aib-L-Phe-OMe 

Relevant articles and documents

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO?) Universal Coupling Reagent for Synthesis in Solution

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO?), a representative member of the inexpensive and environmentally-friendly N-triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO? for peptide synthesis in solution, starting from Z-, Fmoc-, and Boc-protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO? produced high yields, with high crude product purity and low risk of racemization. In all cases, stoichiometric amounts of reagents were used and the standard synthetic procedure, without the need for time-consuming optimization stages or expensive chromatographic purification. DMT/NMM/TsO? was also found to be very useful for the synthesis of oligopeptides using a fragment coupling strategy.

Bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether as coupling reagent for peptide synthesis

Bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether (4) was prepared by treatment of 2-hydroxy-4,6-dimethoxy-1,3,5-triazine with 2-chloro-4,6-dimethoxy-1,3,5- triazine in 61% yield. Ether 4, isoelectronic with pyrocarbonates, was found capable to activate carboxylic acids in the presence of 1,4-diazabicyclo[2.2.2] octane (DABCO) to yield, under mild reaction conditions, superactive triazine esters. Versatility of this new coupling reagent was confirmed by condensation of lipophilic and sterically hindered carboxylic acids with amines in 71-98% yield, and by synthesis of peptides, including those containing Aib-Aib sequence, in solution with high yield and high enantiomeric purity. Copyright

N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis

A new generation of triazine-based coupling reagents (TBCRs), designed according to the concept of "superactive esters", was obtained by treatment of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium (DMTMM) chloride with lithium or silver tetrafluoroborate. The structure of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborate was confirmed by X-ray diffraction. Activation of carboxylic acids by using this reagent proceeds via triazine "superactive ester". The coupling reagent was successfully used for the synthesis of Z-, Boc-, and Fmoc-protected dipeptides derived from natural and unnatural sterically hindered amino acids and for fragment condensation, in 80-100% yield and with high enantiomeric purity. The manual SPPS of the ACP(65-74) peptide fragment (H-Val-Gln-Ala-Ala- lle-Asp-Tyr-Ile-Asn-Gly-OH) proceeded significantly faster than with TBTU or HATU, as well as the automated SPPS of the same fragment gave a purer product than by using TBTU or PyBOP. The reagent was also demonstrated to be efficient in on-resin head-to-tail cyclization of constrained cyclopeptides, in SPPS synthesis of Aib peptides, and in the synthesis of esters from appropriate acids, alcohols, and phenols. The high efficiency and versatility of this new generation of TBCRs confirm, for the first time, the usefulness of the concept of "superactive esters" in rational design of the structure of coupling reagents.