104597-98-0

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyl 2-Methyl (S)-(-)-1,2-Aziridinedicarboxylate is used as a key intermediate for the synthesis of chiral aziridines, which are essential components in the development of various pharmaceuticals. These aziridines are crucial in the creation of anticancer agents, antibiotics, and enzyme inhibitors, making 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE a vital player in the advancement of medical treatments.
Used in Chemical Synthesis:
In the field of chemical synthesis, 1-Benzyl 2-Methyl (S)-(-)-1,2-Aziridinedicarboxylate serves as a valuable chiral building block for the production of complex organic molecules. Its unique structure allows for the creation of a wide range of compounds with specific stereochemistry, which is essential for the development of new drugs and materials with targeted applications.
Used in Research and Development:
1-Benzyl 2-Methyl (S)-(-)-1,2-Aziridinedicarboxylate is also used in research and development laboratories to explore new synthetic pathways and develop innovative methods for the production of chiral aziridines. 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE's versatility and reactivity make it an attractive candidate for the synthesis of novel molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C12H13NO4/c1-16-11(14)10-7-13(10)12(15)17-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3/t10-,13?/m0/s1

Upstream product

• 67-56-1 methanol 
• 1314042-77-7 (4R,7S)-1-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole 
• 64420-86-6 O-p-toluenesulfonyl benzyloxyhydroxamate 
• 107-02-8 acrolein 
• 75154-69-7 (S)-methyl aziridine-2-carboxylate 
• 501-53-1 benzyl chloroformate 
• 75154-68-6 methyl (2S)-N-tritylaziridine-2-carboxylate 

Downstream Products

• 126496-88-6 (S)-2-{[3-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7-hexyl-1H-indol-4-yl]-methyl-amino}-3-methyl-butyric acid methyl ester 
• 245115-63-3 (2S)-2-(benzyloxycarbonylamino)-3-(1,1-dimethylallyloxy)propionic acid methyl ester 
• 887644-53-3 2-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester 
• 887644-54-4 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester 
• 887644-52-2 2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester 
• 868077-89-8 methyl (2R)-N-carbobenzyloxy-β-hydroxyethylcysteineate 
• 96751-61-0 (S)-4-methoxycarbonyl-oxazolidin-2-one 
• 2717-76-2 (S)-N-benzyloxycarbonyl-L-tryptophan methyl ester 
• 1418450-98-2 C₂₀H₂₀N₂O₄ 

Relevant academic research and scientific papers

Synthesis of homochiral acyclic mono- and bis(α-amino acid)s with oligo(oxyethylene) chains

Synthesis of homochiral α-amino acids 3a-3e and bis(α-amino acid)s 4a-4e via BF3·Et2O-catalyzed ring-opening of methyl (S)-1-[(benzyloxy)carbonyl]aziridine-2-carboxylate (7) with oligo(ethylene glycol)s and subsequent acid hydrolysis

IMMUNOPROTEASOME INHIBITORS

Provided herein are compounds, such as a compound of Formula (I), or a pharmaceutically acceptable salt thereof, that are immunoproteasome (such as LMP2 and LMP7) inhibitors. The compounds described herein can be useful for the treatment of diseases treatable by inhibition of immunoproteasomes. Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

Selective cleavage of carbamate protecting groups from aziridines with otera's catalyst

Otera's distannoxane catalyst was found to promote the cleavage of carbamate groups from N-protected aziridines. This method enables the chemoselective cleavage of an aziridinyl N-carbobenzyloxy (Cbz) group in the presence of other N-Cbz groups. The selec

Diastereoselective aziridination of chiral electron-deficient olefins with N-chloro-N-sodiocarbamates catalyzed by chiral quaternary ammonium salts

Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the

Catalytic asymmetric aziridination of α,β-unsaturated aldehydes

The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziri

The in vitro transport of model thiodipeptide prodrugs designed to target the intestinal oligopeptide transporter, PepT1

A thiodipeptide carrier system is shown to be effective at enabling a range of covalently bound molecules, including benzyl, benzoyl and ibuprofen conjugates, to be transported via the intestinal peptide transporter PepT1, demonstrating its potential as a rational drug delivery target.

Stereochemistry of reactions of the inhibitor/substrates L- And D-β-chloroalanine with β-mercaptoethanol catalysed by L-aspartate aminotransferase and D-amino acid aminotransferase respectively

Two members of the α-family of PLP-dependent enzymes, L-aspartate aminotransferase and D-amino acid aminotransferase, have been shown to catalyse β-substitution of L- and D-β-chloroalanine respectively with β-mercaptoethanol, reactions typical of the β-family of PLP-dependent enzymes. The reaction catalysed by L-aspartate aminotransferase has been shown to occur with retention of stereochemistry, a typical outcome for reactions catalysed by β-family enzymes. There are also indications that the reaction catalysed by D-amino acid aminotransferase may involve retention of stereochemistry. Both enzymes have been shown to catalyse exchange at C-3 when the appropriate enantiomer of β-chloroalanine is the substrate. The Royal Society of Chemistry 2005.

Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A

The isolation of the cytotoxic Lissoclinum sp. metabolite trunkamide A was reported in 1996. After completion of a total synthesis in 1999, it became clear that the structure of this marine natural product had to be revised. We now report the first preparation of actual trunkamide A in a total synthesis that serves as an unambiguous structural and stereochemical proof. Highlights of our synthetic strategy are a Lewis acid assisted aziridine opening that was used for the preparation of the novel reverse- prenylated serine and threonine side chains as well as an efficient oxazoline-thiazoline interconversion on the macrocyclic skeleton. In addition, several stereoisomers prepared by complementary synthetic protocols serve to illustrate the general scope of our methodology and confirm the configurational assignment.

Efficient synthesis of (6R)-6-amino-1-methyl-4-(3-methylbenzyl)-hexahydro-1H-1,4-diazepine from methyl (2R)- and (2S)-1-benzyloxycarbonylaziridine-2-carboxylates

An efficient and practical method for the synthesis of (6R)-6-amino-1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepine 2, which serves as the amine part of DAT-582, a potent and selective 5-HT3 receptor antagonist, is described. The key inte

CONSTRUCTION OF OPTICALLY PURE TRYPTOPHANS FROM SERINE DERIVED AZIRIDINE-2-CARBOXYLATES

The possibility of preparing optically pure tryptophan derivatives from various substituted indoles and (2R)- or (2S)-2-aziridinecarboxylates has been examined.Zinc triflate was found to be the only Lewis acid capable of bringing about this reaction in mo