1298023-90-1

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-2-[(Ethylthio)carbonyl]-5-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester is used as a key intermediate in the synthesis of various pharmaceutical compounds for the development of new drugs. Its application is essential in the preparation of rac-Vigabatrin Hydrochloride (V253010), which is an antiepileptic drug used to treat seizures in infants and children. Additionally, it is involved in the synthesis of (-)-Sessilifoliamide C and (-)-8-Epi-stemoamide, which are potential therapeutic agents with various biological activities.

Upstream product

• 53100-44-0 L-N-t-butoxycarbonylpyroglutamic acid 
• 75-08-1 ethanethiol 
• 98-79-3 L-Pyroglutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1298024-11-9 (5S)-pyrrolidin-2-one-5-carbothioic acid ethyl ester 

Downstream Products

• 1428733-28-1 tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate 
• 1428733-29-2 ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate 
• 1428733-31-6 ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate 
• 950690-19-4 ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate 
• 1428733-30-5 (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylic acid 
• 96914-00-0 (S)-5-oxopyrrolidine-2-carbaldehyde 

Relevant academic research and scientific papers

AMIDE DERIVATIVE INHIBITOR AND PREPARATION METHOD AND APPLICATION THEREOF

An amide derivative inhibitor and a preparation method and an application thereof. Specifically relating to the compound shown in general formula (I), a preparation method for same, a pharmaceutical composition comprising said compound, and an application of same as an ASK inhibitor for the treatment of neurodegenerative disease, cardiovascular disease, inflammation, autoimmune and metabolic disease, each of the substituents in the general formula (I) being as defined in the description.

Formal synthesis of (-)-oseltamivir phosphate

The formal synthesis of (-)-oseltamivir phosphate (Tamiflutm) was accomplished starting from (S)-pyroglutamic acid. The synthesis comprised two carbon-carbon bond forming reactions, the first one being a diastereoselective, indium-mediated allylation of a pyroglutamic aldehyde derivative. However, attempts to effect the second carbon-carbon bond formation - cyclohexene ring closure - using an enol-exo aldolization of a dialdehyde resulted in the formation of a product with the opposite regioselectivity. This shortcoming could be overcome by using a reaction sequence of Mannich methylenation/ring-closing metathesis, which provided the desired regioisomer in high yield. Georg Thieme Verlag Stuttgart.New York.

Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide

A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented.