72604-33-2

Upstream product

• 64-17-5 ethanol 
• 1142-20-7 N-Cbz-Ala 
• 71-36-3 butan-1-ol 
• 1115-59-9 (S)-alanine ethyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 18815-73-1 methylzinc iodide 
• 134746-23-9 ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate 
• 4132-86-9 N-benzyloxycarbonylalanine 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 617-27-6 DL-alanine ethyl ester hydrochloride 
• 91806-74-5 3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester 
• 621-84-1 O-benzyl carbamate 
• 16012-70-7 benzyloxycarbonyl-L-alanyl-L-alanine 
• 159390-22-4 1,3-Bis-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-2-ethyl-isourea 

Downstream Products

• 2503-32-4 ethyl N-(benzyloxycarbonyl)-L-alanylglycinate 
• 1142-20-7 N-Cbz-Ala 
• 18323-56-3 Z-(S)-Ala-(S)-Leu-NH₂ 
• 95617-89-3 Z-(S)-Ala-(S)-Phe-NH₂ 
• 3082-75-5 L-Alanine ethyl ester 
• 117402-81-0 n-butyl N-benzyloxycarbonylalaninoate 
• 17350-66-2 N-benzyloxycarbonylalaninehydrazid 
• 1310714-71-6 Cbz-L-Ala-HdHz 
• 1390642-18-8 C₁₅H₁₇NO₄ 
• 183175-43-1 benzyl N-((1S)-2-[(1S)-2-amino-1-(1H-indol-2-ylmethyl)-2-oxoethyl]amino-1-methyl-2-oxoethyl)carbamate 
• 70497-50-6 Z-(S)-Ala-(S)-Val-NH₂ 
• 50444-54-7 benzyl (S)-1-((S)-1-amino-1-oxopropan-2-ylamino)-1-oxopropan-2-ylcarbamate 

Relevant academic research and scientific papers

Asymmetric Synthesis of Protected Unnatural α-Amino Acids via Enantioconvergent Nickel-Catalyzed Cross-Coupling

Interest in unnatural α-Amino acids has increased rapidly in recent years in areas ranging from protein design to medicinal chemistry to materials science. Consequently, the development of efficient, versatile, and straightforward methods for their enanti

Mild construction of 3-methyl tetramic acids enabling a formal synthesis of palau'imide

A general method to construct 3-methyl-4-O-methylated tetramic acids displaying a C-5 stereocenter is presented. The synthetic sequence employs a SmI2-mediated cyclization, whereby the chirality of the emerging tetramic acid core is retained from the starting chiral amino acid. Application to palau'imide is discussed.

Self-assembly and mechanism of L-Alanine-based dihydrazide derivative as excellent gelator of organic solvents

A new organogelator, L-Alanine dihydrazide derivative can self-assemble in various organic solvents and turned them into thermally reversible physical supramolecular organogels at extremely low concentrations ( 2 wt %). The gel-sol phase transition tempe

Combinatorial synthesis of 3,5-Dimethylene substituted 1,2,4-Triazoles

Combinatorial cyclizations of imidates and hydrazides with methylene linked R groups, generated from the corresponding nitriles and carboxylic acids, respectively, provided a large library of 3,5-dimethylene substituted 1,2,4- trizoles. 2011 Bentham Science Publishers Ltd.

Iron-catalyzed four-component reaction for the synthesis of protected primary amines

The first catalytic four-component reaction (4CR) of carbonyl compounds with alkyl chloroformate, HMDS and Et3SiH has been developed to produce protected primary amines by a novel tandem nitrogen protection/direct reductive amination of carbonyl compounds. In the presence of 5 mol-% of an iron(II) salt, a wide variety of aldehydes and ketones were transformed into their corresponding protected primary amines in good to excellent yields under "pure" multicomponent reaction (MCR) conditions. This chemistry was further extended to masked carbonyl compounds such as acetals, ketals, and vinyl ethers. When compared with previous methods to prepare protected primary amines from a large excess of ammonia or ammonium salts, this 4CR not only saved at least one step of synthetic manipulation, but also utilized nearly stoichiometric nitrogen and hydrogen sources and avoided the formation of (protected) secondary amines. Additional advantages of this protocol include broader substrate scope, the use of an inexpensive and environmentally friendly catalyst, and mild reaction conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

A novel tert-butoxycarbonylation reagent: 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)

The use of 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as a tert-butoxycarbonylation reagent for acidic proton-containing substrates such as phenols, aromatic and aliphatic amines hydrochlorides, and aromatic carboxylic acids in the absence of a base is described. The reactions proceed chemoselectively in high yield under mild conditions.

A novel 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)-catalyzed esterification of N-protected amino acids with nearly equimolar amounts of alcohols in the presence of Boc2O

A very mild, BBDI-catalyzed esterification using approximately equimolar amounts of N-protected amino acids and alcohols, in junction with Boc2O is described.

Simple and mild esterification of N-protected amino acids with nearly equimolar amounts of alcohols using 1-tert-butoxy-2-tert-butoxycarbonyl-1,2- dihydroisoquinoline

A very mild, one-step esterification using nearly equimolar amounts of N-protected amino acids and alcohols, in conjunction with 1-tert-butoxy-2-tert- butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as a novel condensing reagent is described.

The role of conformational flexibility of enzymes in the discrimination between amino acid and ester substrates for the subtilisin-catalyzed reaction in organic solvents

To investigate how the conformational flexibility of subtilisin affects its ability to discriminate between enantiomeric amino acid and ester substrates for the subtilisin-catalyzed reaction in an organic solvent, the flexibility around the active site and the surface of subtilisin was estimated from the mobility of a spin label bound to subtilisin by ESR spectroscopy. Many studies on enzyme flexibility focus on the active site. Both the surface and active site flexibility play an important role in the enantioselectivity enhancement of the enzyme-catalyzed reaction. It was found, however, that the different behavior observed for the enantioselectivity between the amino acid and ester substrates could be correlated with the flexibility around the surface rather than the flexibility at the active site of subtilisin. In other words, for the ester substrates, the greater flexibility around the surface of subtilisin induced by a conformational change resulting from the presence of an additive such as DMSO is essential for the enantioselectivity enhancement. This model is also supported by the Michaelis-Menten kinetic parameters for each enantiomeric substrate. Our findings provide insight into the enantioselectivity enhancement for the resolution of enantiomers for enzyme-catalyzed reactions in organic solvents.

Broadening of the substrate tolerance of α-chymotrypsin by using the carbamoylmethyl ester as an acyl donor in kinetically controlled peptide synthesis

In the kinetically controlled approach of peptide synthesis mediated by α-chymotrypsin, the broadening of the protease's substrate tolerance is achieved by switching the acyl donor from the conventional methyl ester to the carbamoylmethyl ester. Thus, as a typical example, the extremely low coupling efficiency obtained by employing the methyl ester of an inherently poor amino acid substrate, Ala, is significantly improved by the use of this particular ester. Its ameliorating effect is observed also in the couplings of other amino acid residues such as Gly and Ser as carboxy components.