24210-19-3

Usage

Uses

Used in Pharmaceutical Synthesis:
CBZ-L-Valine Methyl Ester is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its role is crucial in the development of new drugs and the preparation of existing pharmaceutical products.
Used in Peptide Synthesis:
In peptide synthesis, CBZ-L-Valine Methyl Ester is employed as a protective agent for amino acid residues. This protection is vital for the successful manipulation and synthesis of peptides.
Used in Chemical Production:
CBZ-L-Valine Methyl Ester also serves as a valuable intermediate in the production of other chemicals and compounds, contributing to the versatility and innovation within the chemical industry.

Upstream product

• 186581-53-3 diazomethane 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 28715-70-0 methoxy-phenyl-sulfane 
• 67-56-1 methanol 
• 138754-84-4 N-benzyloxycarbonyl-L-valinal 
• 98807-38-6 Z-L-Val-O-COOMe 
• 30134-65-7 1-Carbobenzoxy-3-i-propylaziridinon 
• 4070-48-8 L-Valine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-51-6 benzyl alcohol 
• 82911-80-6 N-Fmoc-valine methyl ester 
• 7647-01-0 hydrogenchloride 
• 124-38-9 carbon dioxide 
• 6306-52-1 L-valine methylester hydrochloride 

Downstream Products

• 2443-71-2 benzyl (S)-(1-hydrazineyl-3-methyl-1-oxobutan-2-yl)carbamate 
• 6216-65-5 N-benzyloxycarbonyl-L-valinol 
• 118209-08-8 Z-Val-Gly-D-Leu-OMe 
• 53941-41-6 Z-Val-D-Leu-OMe 
• 123411-89-2 ((1S,2R)-2-Hydroxy-1-isopropyl-pent-4-enyl)-carbamic acid benzyl ester 
• 123411-90-5 ((1S,2S)-2-Hydroxy-1-isopropyl-pent-4-enyl)-carbamic acid benzyl ester 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 191731-16-5 (S)-tert-butyl 4-(benzyloxycarbonyl)amino-5-methyl-3-oxohexanoate 
• 66866-64-6 (4S)-4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 850796-29-1 dimethylsulfoxonium (3S)-2-oxo-3-(benzyloxycarbonylamino)-4-methylpentylide 
• 138754-84-4 N-benzyloxycarbonyl-L-valinal 
• 137719-71-2 (S)-2-<(benzyloxycarbonyl)amino>-3-methylbutyl ethanethioate 
• 174872-56-1 n-butyl N-benzyloxycarbonylvalinoate 
• 1390642-19-9 C₁₇H₂₁NO₄ 

Relevant academic research and scientific papers

An Atom-Economic Inverse Solid-Phase Peptide Synthesis Using Bn or BcM Esters of Amino Acids

An atom-economic N-to-C-directed solid-phase peptide synthesis is reported that uses benzyl (Bn) or (benzhydryl-carbamoyl)-methyl (BcM) esters of amino acids as the building blocks, which facilitate efficient hydrazinolysis, convenient conversion to acyl azide, and robust amidation with the next amino acid ester. This method is free of coupling reagents and free of protection on the side-chain OH, CO2H, CONH2, etc., therefore exhibiting a significantly improved atom economy compared to those of BOC- or Fmoc-based C-to-N-directed approaches.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds

Herein, we describe the development of a simple, high yielding and stereocontrolled strategy for the synthesis of a series of triazolopiperazines and other biologically relevant fused scaffolds from optically active amino acids. This route was applied to the synthesis of 22 scaffolds containing new, previously inaccessible vectors and used to access a novel analogue of ganaplacide.

α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation

Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine.

PEPTIDOMIMETIC COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF

This invention relates to peptidomimetic linkers and anti-body drug conjugates thereof, to pharmaceutical compositions containing them, and to their use in therapy for the prevention or treatment of cancer.

Synthesis and applications in Henry reactions of novel chiral thiazoline tridentate ligands

Several novel chiral tridentate ligands containing thiazoline were efficiently synthesized from commercially available l=cysteine in high yield. These ligands were subsequently applied to the asymmetric Henry reaction of nitromethane and various aldehydes. It was found that the structures of the thiazoline ligands had a significant influence on the enantioselectivity. It was shown that the optimal catalyst for this reaction was a ligand complexed with CuCl, which was formed from chiral thiazoline with chiral aminoalcohol. At -20°C, with 10 mol% of this ligand, a product with (S)-configuration was isolated in 93% yield and 98% enantiomeric excess.

N-Urethane protection of amines and amino acids in an ionic liquid

An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.

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.

A favorable, narrow, δh Hansen-parameter domain for gelation of low-molecular-weight amino acid derivatives

In recent years, the design of new low-molecular-weight gelators (LMWGs) has attracted considerable attention because of the interesting supramolecular architectures as well as industrial applications. In this context, the role of the organic solvent in d

PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED AMINO-ALCOHOLS

A process for preparing an enantiomerically enriched amino alcohol or derivatives thereof having the structure: wherein C* is a chiral carbon atom and R1 and R2 are independently selected from hydrogen, alkyl, alkoxy, aryl and a peptide chain, wherein said process includes the steps of: (a) providing an amino acid having the structure of Formula I: (b) protecting the amino group of the Formula I amino acid with a carbobenzoxy(Cbz) N-protecting group by reacting the amino acid with benzyl chloroformate in the presence of a base; (c) forming a carboxylic acid alkyl ester of the Cbz N-protected Formula I amino acid by reacting the amino acid with a C1-12 alcohol; and (d) reducing the Cbz N-protected amino acid ester with a borohydride reducing agent in an organic solvent or mixture of organic solvents to form a Cbz N-protected amino-alcohol