92136-57-7

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-BOC-2-AMINO-5-HEXENOIC ACID METHYL ESTER is used as a building block for the synthesis of peptide-based drugs and pharmaceuticals. Its BOC protecting group allows for selective manipulation in reactions, making it a valuable component in the development of new medications.
Used in Organic Synthesis:
(2S)-BOC-2-AMINO-5-HEXENOIC ACID METHYL ESTER is used as a key intermediate in the synthesis of various organic compounds. Its unique structure and BOC protecting group make it a versatile component in the creation of complex organic molecules.

Upstream product

• 74-88-4 methyl iodide 
• 122471-00-5 acetylamino-3-butenyl-propanedioic acid diethyl ester 
• 141943-64-8 (±)-2-acetamidohex-5-enoic acid 
• 170848-34-7 methyl 2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate 
• 107-05-1 3-chloroprop-1-ene 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 410098-01-0 (2S)-2-aminohex-5-enoic acid methyl ester 
• 263023-29-6 (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid methyl ester 
• 62019-06-1 (E)-2,6-heptadien-1-ol 
• 263023-28-5 (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid 
• 101650-17-3 (S)-2-amino-4-bromobutyric acid methyl ester 
• 170848-34-7 N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester 
• 106-95-6 allyl bromide 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 214206-61-8 2-tert-butoxycarbonylamino-hex-5-enoic acid 
• 208522-13-8 (S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid 
• 225779-17-9 tert-butyl N-[(1S)-1-(hydroxymethyl)pent-4-enyl]carbamate 
• 916154-72-8 methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate 
• 873017-34-6 {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester 
• 624743-18-6 N-butoxycarbonyl homoallylglycinal 
• 851909-03-0 N-(N-(Boc)-L-homoallylglycyl)-N-(2,4-dimethoxybenzyl)-L-allylglycine methyl ester 
• 851909-06-3 N-(N-(Boc)-L-homoallylglycyl)-N-(2-hydroxy-4-methoxybenzyl)-L-homoallylglycine methyl ester 
• 851909-05-2 N-(N-(Boc)-L-homoallylglycyl)-N-(2,4-dimethoxybenzyl)-L-homoallylglycine methyl ester 
• 81505-49-9 (S)-(-)-Methyl 2-[(tert-butoxycarbonyl)amino]-6-hydroxypentanoate 

Relevant academic research and scientific papers

MODULATORS OF THE INTEGRATED STRESS RESPONSE PATHWAY

The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts, solvates, hydrates, tautomers or stereoisomers thereof, wherein R1 to R3, A1 and A2 have the meaning as indicated in the description and claims. The invention further relates to pharmaceutical compositions comprising said compounds, their use as medicament and in a method for treating and preventing one or more diseases or disorders associated with integrated stress response.

Aliphatic chain-containing macrocycles as diazonamide A analogs

[Figure not available: see fulltext.] Aliphatic alkyl chain-containing 12–14-membered macrocycles have been designed as structural analogs of antimitotic natural product diazonamide A. Macrocycles were synthesized from 5-bromooxazole in 7 to 9 linear step

MODULATORS OF THE INTEGRATED STRESS PATHWAY

Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases; disorders and conditions.

Z-SELECTIVE OLEFIN METATHESIS OF PEPTIDES

The invention relates generally to the synthesis of modified amino acids and modified peptides in the presence of cyclometalated catalysts. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine

Synthesis of ω-Oxo Amino Acids and trans-5-Substituted Proline Derivatives Using Cross-Metathesis of Unsaturated Amino Acids

A range of 7-oxo, 8-oxo, and 9-oxo amino acids, analogues of 8-oxo-2-aminodecanoic acid, one of the key components of the cyclic tetrapeptide apicidin, have been prepared by a three-step process involving copper-catalyzed allylation of serine-, aspartic acid-, and glutamic acid-derived organozinc reagents, followed by cross-metathesis of the resulting terminal alkenes with unsaturated ketones and hydrogenation. The intermediate 7-oxo-5-enones underwent a highly diastereoselective (dr ≥96:4) acid-catalyzed aza-Michael reaction to give trans-2,5-disubstituted pyrrolidines, 5-substituted proline derivatives. The aza-Michael reaction was first observed when the starting enones were allowed to stand in solution in deuterochloroform but can be efficiently promoted by catalytic amounts of dry HCl.

Insight into Transannular Cyclization Reactions to Synthesize Azabicyclo[X.Y.Z]alkanone Amino Acid Derivatives from 8-, 9-, and 10-Membered Macrocyclic Dipeptide Lactams

An efficient method for synthesizing different functionalized azabicyclo[X.Y.0]alkanone amino acid derivatives has been developed employing electrophilic transannular cyclizations of 8-, 9-, and 10-membered unsaturated macrocycles to form 5,5-, 6,5-, 7,5-, and 6,6-fused bicylic amino acids, respectively. Macrocycles were obtained by a sequence featuring peptide coupling of vinyl-, allyl-, homoallyl-, and homohomoallylglycine building blocks followed by ring-closing metathesis. X-ray crystallographic analyses of the 8-, 9-, and 10-membered macrocyclic lactam starting materials as well as certain bicyclic amino acid products provided insight into their conformational preferences as well as the mechanism for the diastereoselective formation of specific azabicycloalkanone amino acids by way of transannular iodolactamization reactions. (Chemical Equation Presented).

Z-selective olefin metathesis on peptides: Investigation of side-chain influence, preorganization, and guidelines in substrate selection

Olefin metathesis has emerged as a promising strategy for modulating the stability and activity of biologically relevant compounds; however, the ability to control olefin geometry in the product remains a challenge. Recent advances in the design of cyclom

Synthesis of the unusual α-amino acid component of some novel histone deacetylase inhibiting cyclic peptides

A flexible protocol for the synthesis of three lipophilic α-amino acid components of some novel cyclic peptides having important histone deacetylase inhibiting properties has been developed from a common source, which featured a cross-metathesis reaction

Flexible synthesis and evaluation of diverse anti-apicomplexa cyclic peptides

A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon-nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.

New histone deacetylase inhibitors based on 4-fluoro-2-amino acid esters: Synthesis and activity

A series of twelve fluorinated and non-fluorinated potential histone deacetylase inhibitors 25 was synthesized and their inhibitory activity was tested against rat liver histone deacetylase. The new inhibitors involve an enzyme binding element consisting of asparagine, glutamine or different short chain fluorinated or unfluorinated amino acids, a suberoyl spacer and a hydroxamic acid functionality, which is responsible for the inhibitory activity. The 4-fluoro-2-aminobutyric acid esters 1a,b, their 2-methyl derivatives 2a,b and the 2-amino-4-fluoropent-4-enoic acid esters 3a,b were synthesized by alkylation of glycine or alanine ester imides with bromofluoroethane or 2-fluoroallylbromide, respectively. Methyl 2-amino-5-fluorohex-5-enoate (4a) was prepared using 3-fluorobut-3-enyl tosylate or the iodide as alkylating reagents. An alternative pathway starting from Boc protected 3-iodo-L-alanine was more efficient. The latter method was also applied to synthesize the parent unfluorinated compound 4c using allylbromide as the alkylating reagent. The fluorinated compounds, tested as histone deacetylase inhibitors were slightly less active than comparable (S)-valine, (S)-phenylalanine or (S)-allylglycine derivatives that do not contain a fluorine atom. Interestingly, it was shown for the first time that the fluoro vinyl group which was proposed to be an aprotic amide mimic due to its electronic properties may serve as a bioisosteric replacement of a primary amide function. For the fluorinated analogs 25f (IC50 0.88 μM) and 25i (IC50 1.02 μM) a similar or an even enhanced inhibitory activity was observed compared to the unfluorinated parents 25g (IC50 0.67 μM) and 25j (IC50 1.79 μM) or the (S)-asparagine or (S)-glutamine derivatives 25l (IC50 2.10 μM) and 25m (IC50 3.90 μM).