208522-13-8

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-N-Boc-2-(3'-butenyl)glycine is used as a building block for the synthesis of various pharmaceuticals and bioactive molecules. Its unique structure allows for the creation of complex molecules with specific functional groups, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-N-Boc-2-(3'-butenyl)glycine is used as a versatile intermediate for the preparation of a wide range of organic compounds. The Boc protecting group facilitates selective reactions, while the 3'-butenyl group enables the introduction of specific functional groups in a controlled manner.
Used in Research and Development:
(S)-N-Boc-2-(3'-butenyl)glycine is utilized in research and development for the exploration of new synthetic pathways and the discovery of novel chemical compounds. Its unique properties make it a valuable tool for scientists working on the frontiers of organic chemistry and drug development.

Upstream product

• 200405-38-5 ethyl L-2-amino-5-hexenoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 90989-12-1 (2S)-2-amino-5-hexenoic acid 
• 226985-05-3 (S)-(-)-1-tert-butyl-2--5-hexenoate 
• 144090-57-3 tert-butyl (S)-4-(but-3-enyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 756498-97-2 (RS)-ethyl 2 N-(tert-butoxycarbonyl)-2-amino-5-hexenoate 
• 102831-44-7 diethyl tert-butoxycarbonylaminomalonate 
• 410098-01-0 (2S)-2-aminohex-5-enoic acid methyl ester 
• 188177-79-9 (2R,5S)-5-(But-3-enyl)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 194656-73-0 (S)-1-tert-butyl 2-[bis-(tert-butoxycarbonyl)amino]-5-oxopentanoate 
• 197159-25-4 N-tert-butoxycarbonyl-L-glutamic acid α-tert-butyl ester γ-N-methoxy-N-methylamide 
• 145037-74-7 (S)-(-)-1-tert-butyl-2-<(tert-butoxycarbonyl)amino>-5-hexenoate 

Downstream Products

• 1426343-22-7 C₃₆H₅₀N₈O₅ 
• 1426343-13-6 C₃₆H₅₀N₈O₅ 
• 1433856-33-7 C₂₀H₂₇N₃O₂*ClH 
• 92136-57-7 (S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester 

Relevant academic research and scientific papers

Methylene Analogues of Neopetrosiamide as Potential Antimetastatic Agents: Solid-Supported Syntheses Using Diamino Diacids for Pre-Stapling of Peptides with Multiple Disulfides

Neopetrosiamide, a 28-residue peptide from Neopetrosia sp., contains three disulfide bonds and hinders mammalian tumor cell invasion. Proper connectivity of disulfide bonds is crucial for activity. Synthetic replacement of single disulfide bridges with methylene bridges gives active analogues. Pre-stapling of one ring enhances the correct formation of the remaining disulfides by reducing isomeric possibilities and possibly initiating the correct 3D fold. Cloning and expression of neopetrosiamide in E. coli affords access to the natural linear peptide.

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

Novel multi-target azinesulfonamides of cyclic amine derivatives as potential antipsychotics with pro-social and pro-cognitive effects

Currently used antipsychotics are characterized by multireceptor mode of action. While antagonism of dopamine D2 receptors is responsible for the alleviation of “positive” symptoms of schizophrenia and the effects at other, particularly serotonergic receptors are necessary for their additional therapeutic effects, there is no consensus regarding an “ideal” target engagement. Here, a detailed SAR analysis in a series of 45 novel azinesulfonamides of cyclic amine derivatives, involving the aryl-piperazine/piperidine pharmacophore, central alicyclic amine and azinesulfonamide groups has led to the selection of (S)-4-((2-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)pyrrolidin-1-yl)sulfonyl)isoquinoline (62). The polypharmacology profile of 62, characterized by partial 5-HT1AR agonism, 5-HT2A/5-HT7/D2/D3R antagonism, and blockade of SERT, reduced the “positive”-like, and “negative”-like symptoms of psychoses. Compound 62 produced no catalepsy, demonstrated a low hyperprolactinemia liability and displayed pro-cognitive effects in the novel object recognition task and attentional set-shifting test. While association of in vitro features with the promising in vivo profile of 62 is still not fully established, its clinical efficacy should be verified in further stages of development.

Synthesis of an Uncharged Tetra-cyclopeptide Acting as a Transmembrane Carrier: Enhanced Cellular and Nuclear Uptake

A small uncharged cyclopeptide scaffold inspired by a natural product and designed to undergo postfunctionalizations was used as a new transmembrane vector. A bioactive and fluorescent triazole aminocoumarin was bound to this carrier to facilitate its mov

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).

α-Chymotrypsin and l-acylase aided synthesis of 5-hydroxypipecolic acid via Jacobsen's hydrolytic kinetic resolution of epoxy amino acids

Diethyl malonate derivatives were used to synthesize racemic 2-amino-5-hexenoic acid. These racemic 2-amino-5-hexenoic acid (homoallylyglycine) derivatives were efficiently resolved aided by α-chymotrypsin or l-acylase, giving rise to l- and d-enantiomers

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.

CYCLIC PEPTIDES WITH AN ANTI-PARASITIC ACTIVITY

The present invention relates to a method for preparing a cyclic peptide with antiparasite activity and anticancer activity. The invention also relates to this peptide as an antiparasite agent, for example in the treatment of toxoplasmosis and as an antic

Synthesis of macrocyclic trypanosomal cysteine protease inhibitors

The importance of cysteine proteases in parasites, compounded with the lack of redundancy compared to their mammalian hosts makes proteases attractive targets for the development of new therapeutic agents. The binding mode of K11002 to cruzain, the major cysteine protease of Trypanosoma cruzi was used in the design of conformationally constrained inhibitors. Vinyl sulfone-containing macrocycles were synthesized via olefin ring-closing metathesis and evaluated against cruzain and the closely related cysteine protease, rhodesain.