915317-20-3

Usage

Uses

Used in Organic Synthesis:
(1R,2R)-Methyl 1-(tert-butoxycarbonylaMino)-2-vinylcyclopropanecarboxylate is used as a reagent for the preparation of various cyclopropane derivatives, enabling the creation of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (1R,2R)-Methyl 1-(tert-butoxycarbonylaMino)-2-vinylcyclopropanecarboxylate is used as a key intermediate in the synthesis of drugs, contributing to the development of new medications.
Used in Agrochemical Production:
Similarly, in agrochemicals, (1R,2R)-Methyl 1-(tert-butoxycarbonylaMino)-2-vinylcyclopropanecarboxylate is utilized as a precursor for the synthesis of various agrochemical products, supporting agricultural advancements.
The tert-butoxycarbonyl-protected amino group in (1R,2R)-Methyl 1-(tert-butoxycarbonylaMino)-2-vinylcyclopropanecarboxylate plays a crucial role as a protecting group, allowing for selective reactions at other parts of the molecule, which is essential for achieving specific molecular structures in the synthesis of target compounds.

Upstream product

• 159622-08-9 (1S,2S)-1-Azidocarbonyl-2-vinyl-cyclopropanecarboxylic acid methyl ester 
• 75-65-0 tert-butyl alcohol 
• 67-56-1 methanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 213316-32-6 rac-(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester 
• 17447-60-8 dimethyl 2-vinylcyclopropane-1,1-dicarboxylate 
• 159700-58-0 (1R,2S)-2-vinyl-1-aminocyclopropanecarboxylic acid 
• 159622-10-3 (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 159622-09-0 (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester 
• 1185537-10-3 (1S,2R)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester 
• 6974-12-5 1,4-dibromo-2-butene 
• 66646-88-6 (E)-N-benzylideneglycine methyl ester 
• 213316-49-5 (1RS,2SR)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate 

Downstream Products

• 853269-57-5 tert-butyl [(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]carbamate 

Relevant academic research and scientific papers

A TEIXOBACTIN ANALOGUE AND USE THEREOF

Provided herein belongs to the field of pharmaceuticals, and specifically relates to a Teixobactin analogue and use thereof. It further relates to a pharmaceutical composition comprising the compound and use of the compound and the pharmaceutical composit

Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained α-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step SN2 and SN2′ alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA.

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2-SN2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex

This work describes a new process for the asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid of high pharmaceutical importance. The sequence of the reactions includes PTC alkylation (SN2), homogeneous SN2′ cyclization followed by disassembly of the resultant Ni(ii) complex. All reactions are conducted under operationally convenient conditions and suitably scaled up to 6 g of the starting Ni(ii) complex. This journal is

Synthesis of methyl-1-(tert -butoxycarbonylamino)-2- vinylcyclopropanecarboxylate via a hofmann rearrangement utilizing trichloroisocyanuric acid as an oxidant

A trichloroisocyanuric acid (TCCA) mediated Hofmann rearrangement was utilized to synthesize methyl-1-(tert-butoxycarbonylamino)-2- vinylcyclopropanecarboxylate. A variety of functional groups are tolerated in this reaction including vinyl, cyclopropyl, pyridyl, aryl, benzyl, and nitro groups.

Inhibitors of Serine Proteases

The present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention.

MACROCYCLIC HEPATITIS C PROTEASE INHIBITORS

The present invention provides novel macrocyclic compounds that mimic peptide substrates of the hepatitis C viral protease and inhibit the viral protease, more particularly as inhibitors of the NS3 serine protease from hepatitis C virus. Methods for synthesis of the compounds are also provided. The compounds find utility as antiviral agents directed at hepatitis C. The invention further provides methods of employing such inhibitors, alone or in combination with other therapeutic agents, to treat hepatitis C infection in a subject in need of such treatment.

INHIBITORS OF SERINE PROTEASES FOR THE TREATMENT OF HCV INFECTIONS

The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt thereof. These compounds inhibit serine protease, particularly the hepatitis C virus NS3-NS4A protease.

INHIBITORS OF SERINE PROTEASES

The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt or mixtures thereof that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease.

A PROCESS FOR RESOLVING RACEMIC MIXTURES AND A DIASTEREOISOMERIC COMPLEX OF A RESOLVING AGENT AND AN ENANTIOMER OF INTEREST

A process for resolving a compound in racemic form comprising the following steps is described: a) reacting a compound in racemic form with a resolving agent, b) forming a diastereoisomeric complex of the resolving agent and an enantiomer of interest, c} separating the enantiomer of interest from the obtained diastereoisomer, wherein such a process is characterized in that said resolving agent is a compound of Formula (I). A diastereoisomeric complex between the resolving agent of Formula (I) and the enantiomer of interest is also described. The process according to the invention allows acid and basic racemic mixtures to be separated.

Epimerization reaction of a substituted vinylcyclopropane catalyzed by ruthenium carbenes: Mechanistic analysis

A novel ruthenium carbene-catalyzed epimerization of vinylcyclopropanes is reported. The reaction rate strongly depends on the presence of ruthenium ligands in solution. When the first-generation Grubbs catalyst is employed, a 5.3:1 equilibrium ratio of epimers is established quickly, but when a first-generation Hoveyda catalyst is employed, epimerization is observed only if an additional phosphine or nitrogen ligand is added. NMR and kinetic studies suggest that the isomerization reaction occurs through the intermediacy of a ruthenacyclopentene. The observation suggests that cyclopropylmethylidene ruthenium carbenes of synthetic utility may be accessible via ruthenacyclopentenes obtained via other routes.