6671-25-6

Basic information

• Product Name: Alanine, 2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]alanyl]-, methyl ester
• CAS NO: 6671-25-6
• Molecular Formula: C17H24N2O5
• Molecular Weight: 336.388
• Mol File: 6671-25-6.mol
• Article Data: 27

Chemical Properties

• CAS DataBase Reference: Alanine, 2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]alanyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Alanine, 2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]alanyl]-, methyl ester(6671-25-6)
• EPA Substance Registry System: Alanine, 2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]alanyl]-, methyl ester(6671-25-6)

Safety Data

• Hazardous Substances Data: 6671-25-6(Hazardous Substances Data)

Upstream product

• 13257-67-5 2-amino-2-methylpropionic acid methyl ester 
• 15030-72-5 Z-Aib-OH 
• 15030-73-6 Z-Aib-oPiv 
• 39608-52-1 benzyl carbonochloridate 
• 67-56-1 methanol 
• 79775-03-4 2-<2-(Benzyloxycarboxamido)-2-methylpropionamido>-2-methylpropionsaeure 
• 15028-41-8 methyl 2-aminoisobutyrate hydrochloride 
• 367274-56-4 Z-Aib-F 
• 501-53-1 benzyl chloroformate 
• 15030-74-7 (Z-Aib)2O 

Downstream Products

• 79775-03-4 2-<2-(Benzyloxycarboxamido)-2-methylpropionamido>-2-methylpropionsaeure 
• 4512-46-3 3,3,6,6-tetramethyl-2,5-dioxopiperazine 
• 87208-84-2 H₂N-(Aib)2-OMe 
• 132329-83-0 Z-Pro-Val-Aib-Aib-Gln-Gln-Pheol 
• 96235-56-2 L-Pro-L-Val-Aib-Aib-L-Gln-L-Gln-L-Phl 
• 132329-82-9 Z-Ala-Ala-Ala-Aib-Aib-OMe 
• 132329-81-8 Z-Ala-Aib-Aib-OMe 
• 71890-87-4 N-phenylmethoxycarbonyl-L-prolyl-L-valyl-2-methylalanyl-2-methylalanine 
• 109335-02-6 N,N-dibenzyl-O-tert-butyltyrosyl-α-aminoisobutyryl-α-aminoisobutyrylmelphalanylleucine tert-butyl ester 
• 109334-90-9 N,N-dibenzyltyrosyl-α-aminoisobutyryl-α-aminoisobutyrylmelphalanylleucine 
• 109335-01-5 N,N-diallyl-O-tert-butyltyrosyl-α-aminoisobutyryl-α-aminoisobutyrylmelphalanylleucine tert-butyl ester 
• 109335-06-0 N,N-dibenzyl-O-tert-butyltyrosyl-α-aminoisobutyryl-α-aminoisobutyrylphenylalanylleucine tert-butyl ester 
• 109334-89-6 N,N-diallyltyrosyl-α-aminoisobutyryl-α-aminoisobutyrylmelphalanylleucine 
• 109335-03-7 N,N-dibenzyltyrosyl-α-aminoisobutyryl-α-aminoisobutyrylphenylalanylleucine 

Relevant articles and documents

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

Peptide Mechanosynthesis by Direct Coupling of N-Protected α-Amino Acids with Amino Esters

In view of developing alternatives to classical peptide synthesis strategies that suffer from low efficacy and negative environmental impact, the reactivity of N-protected α-amino acids, amino esters, and N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide was

The effect of counterion and tertiary amine on the efficiency of N-triazinylammonium sulfonates in solution and solid-phase peptide synthesis

A collection of N-triazinylammonium sulfonates, designed according to the concept of "superactive esters", was obtained by treatment of ammonium sulfonates with 2-chloro-4,6-dimethoxy-1,3,5-triazine. The structure of the tertiary amine as well as sulfonate anion influenced their reactivity and stability in N,N-dimethylformamide (DMF) solution. The reagents were successfully used in solution- and solid-phase synthesis of Z-, Boc-, and Fmoc-protected peptides containing natural and unnatural sterically hindered amino acids as well as in [2+1] fragment condensation approaches, yielding the final products in 80-100% yield and high optical purity. In manual SPPS of the [Aib]2[Aib]4-enkephalin analogue and the ACP(65-74) peptide fragment VQAAIDYINEG, several sulfonates yielded peptides significantly faster than TBTU or HATU. Comparative analyses demonstrated that 4-(4,6-di-methoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium 4-toluenesulfonate was the most versatile reagent in a wide range of coupling procedures.