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

• 16258-05-2 D,L-2-amino-5-hexenoic acid 
• 170848-34-7 methyl 2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate 
• 107-05-1 3-chloroprop-1-ene 
• 186581-53-3 diazomethane 
• 208522-13-8 (S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid 
• 2100-17-6 4-pentenal 
• 170848-34-7 N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester 
• 106-95-6 allyl bromide 
• 74-88-4 methyl iodide 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 101650-17-3 (S)-2-amino-4-bromobutyric acid methyl ester 
• 188177-79-9 (2R,5S)-5-(But-3-enyl)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 
• 263023-23-0 (2S,3S)-3-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]hept-5-en-1,2-diol 

Downstream Products

• 208522-13-8 (S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid 
• 916154-72-8 methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate 
• 1247053-03-7 (-)-S-{4-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]butyl} ethanethioate 
• 1247052-63-6 C₃₃H₅₀N₄O₇ 
• 1247052-65-8 (-)-(3S,9S,14aR)-9-benzyl-3-(but-3-enyl)-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone 
• 1247052-85-2 S-{1-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]-7-chloro-6-oxoheptan-3-yl} O-ethyl carbonodithioate 
• 104849-07-2 (-)-(3S,9S,14aR)-9-benzyl-3-(7-chloro-6-oxoheptyl)-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone 
• 887277-67-0 (3S,9S,14aR)-9-benzyl-3-(7-bromo-6-oxoheptyl)-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone 
• 1247053-17-3 S-7-((3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl)-2-oxoheptyl O-ethyl carbonodithioate 
• 881657-99-4 tert-butyl ((3S,6R)-6-(((1-phenyl-1H-tetrazol-5-yl)sulfonyl)-methyl)tetrahydro-2H-pyran-3-yl)carbamate 
• 881657-57-4 C₁₈H₂₇NO₆S 
• 851909-11-0 methyl (2S)-2-[(2,4-dimethoxybenzyl)amino]hex-5-enoate 
• 851909-00-7 N-(N-(Boc)-allylglycyl)-N-(2,4-dimethoxybenzyl)homoallylglycine methyl ester 
• 851909-01-8 N-(N-(Fmoc)-L-allylglycyl)-N-(2,4-dimethoxybenzyl)-L-homoallylglycine methyl ester 

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

Native chemical ligation, thiol-ene click: A methodology for the synthesis of functionalized peptides

The sequential combination of native chemical ligation and thiol-ene radical chemistry (NCL-TEC) on the resulting cysteine thiol has been investigated as a methodology for rapidly accessing functionalized peptides. Three sequential cycles of native chemical ligation and subsequent thiyl radical reactions (including a free-radical-mediated desulfurization reaction) were carried out on a peptide backbone demonstrating the iterative nature of this process. The versatility of the thiyl radical reaction at cysteine was demonstrated through the introduction of a number of different side chains including an amino acid derivative, a carbohydrate group, and an alkyl azide. Conditions were developed that allowed the sequential NCL-TEC process to proceed in high yield.

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.