80442-95-1

Usage

InChI:InChI=1/C7H11NO2S/c1-2-10-7(9)5-3-4-6(11)8-5/h5H,2-4H2,1H3,(H,8,11)/t5-/m0/s1

Upstream product

• 7149-65-7 ethyl (S)-pyroglutamate 
• 56-86-0 L-glutamic acid 

Downstream Products

• 1421277-03-3 (S)-ethyl 5-((2-oxo-2-phenylethyl)thio)-3,4-dihydro-2H-pyrrole-2-carboxylate 
• 1621003-90-4 (S)-ethyl 5-(4,4-dimethyl-2,6-dioxocyclohexylidene)pyrrolidine-2-carboxylate 
• 1421276-96-1 (S)-ethyl 5-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-ylidene)pyrrolidine-2-carboxylate 
• 1421277-01-1 (S)-ethyl 5-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-ylidene)pyrrolidine-2-carboxylate 
• 1353674-41-5 (S)-dimethyl 2-(5-(ethoxycarbonyl)pyrrolidin-2-ylidene)malonate 
• 1353674-43-7 (S)-ethyl 5-((2-ethoxy-2-oxoethyl)thio)-3,4-dihydro-2H-pyrrole-2-carboxylate 
• 623-91-6 diethyl Fumarate 
• 468096-97-1 ethyl (3S,5aR)-tetrahydropyrrolo[1,2-b]oxaziridine-3-carboxylate 
• 468096-98-2 ethyl (3S,5aS)-tetrahydropyrrolo[1,2-b]oxaziridine-3-carboxylate 
• 172879-74-2 ethyl (S)-3,4-dihydro-2H-pyrrole-2-carboxylate 
• 908366-29-0 (2S,5S)-N-benzoyl-5-(1,1-di(ethoxycarbonyl)ethyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 908365-91-3 (2S,5S)-N-benzoyl-5-(di(ethoxycarbonyl)methyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 675588-13-3 (2S,5R)-N-benzoyl-5-(di(ethoxycarbonyl)methyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 142890-15-1 (S)-diethyl 2-(2-((tert-butyldiphenylsilyloxy)methyl)pyrrolidin-5-ylidene)malonate 

Relevant academic research and scientific papers

Concise enantiospecific synthesis of a coccinellied alkaloid, (-)-adalinine.

[reaction: see text] An enantiospecific synthesis of a coccinellied alkaloid, (-)-adalinine, was established starting from (S)-(-)-pyroglutamic acid, where a stereoselective Michael addition and a samarium iodide-promoted regioselective carbon-nitrogen bond cleavage reaction were involved as the key reactions.

Synthetic studies towards the core structure of nakadomarin a by a thioamide-based strategy

The tricyclic BCD substructure of the marine natural product nakadomarin A has been synthesised. The strategy utilised a key carbon-carbon bond-forming reaction between a furan and an N-acyliminium ion derived from a secondary thiolactam. In addition, a novel three-component coupling reaction between a thioamide, an allylic bromide and an isocyanate, leading to the establishment of two new stereogenic centres, is reported. Two key steps in a projected total synthesis of nakadomarin A have been realised by using the unique chemistry of thioamides. Formation of the carbocyclic B ring can be effected by nucleophilic attack of a furan on a thiolactam-derived iminium ion, and the key quaternary centre can be established by a novel three-component coupling reaction.

2,5-Disubstituted pyrrolidines: Synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations

Methodology for the diastereoselective synthesis of 2,5-disubstituted pyrrolidines by reduction of enamines derived from pyroglutamic acid is reported; the nature of nitrogen protection was found to be critical for the stereochemical control of the reaction outcome. Regioselective manipulation of the C-2 and C-5 substituents is possible, providing access to differently substituted pyrrolidines for a limited number of cases. The Royal Society of Chemistry 2006.

Photoswitchable elements within a peptide backbone-ultrafast spectroscopy of thioxylated amides

A series of thioxo compounds, thioacetamide, N-methylthioacetamide, a cyclic thioxoamide [(S)-5-thioxopyrrolidine-2-carboxylic acid ethyl ester], two thioxylated dipeptides (Ala-Ψ[CS-NH]-Ala and Phe-Ψ[CS-NH]-Ala) and a thioxylated dodecapeptide (Lys-Glu-Thr-Ala-Ala-Ala-Lys-Phe-Glu-Arg-Gln-His- Ψ[CS-NH]-Nle-Asp-Ser-Ser-Thr-Ser-Ala-Ala, or [thioxo-His12]-S- peptide; Nle = norleucine) are investigated by ultrafast spectroscopy in the visible and near UV. The different molecules show very similar absorption dynamics featuring a rise of a strong visible absorption band on the subpicosecond and picosecond time scale. The decay of the visible absorption occurs within 150-600 ps. The observations are interpreted by the ultrafast formation of triplet states and their decay on the subnanosecond time scale. Comparison with published ER experiments on N-methylthioacetamide indicates that the cis-trans isomerization around the thioxopeptide bond is terminated within less than 1 ns.

Studies towards the total synthesis of batzelladine A

Application of a diastereoselective three-component coupling to the bicyclic core of the batzelladine alkaloids is described. The synthesis features the elaboration of glutamic acid by use of Eschenmoser sulfide contraction. An earlier approach is also included, which shows some limitations of dithiane chemistry when applied to the particular compounds required for this target.

Studies towards the total synthesis of Batzelladine A: Synthesis of a model pyrrolo[1,2-c]pyrimidine

A new approach to the synthesis of fragments related to the batzelladine alkaloids has been developed using a formal asymmetric aza-Diels-Alder reaction.

Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide

A convenient synthesis of the title nitrone is reported. The sequence starts from ethyl L-pyroglutamate as the source of chirality and the key step is the generation of an unstable α-methoxy-N-carboxylate ion, which readily decomposes to an imine. The oxidation of the imine with methyl(trifluoromethyl)dioxirane provides the enantiopure nitrone, which is trapped with dimethyl acetylenedicarboxylate.

Synthesis of (S)-3,4-Dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-Oxide

The synthesis of a series of new enantiopure 3,4-dihydro-2H-pyrrole derivatives including the title nitrone and its cycloaddition product to dimethyl acetylenedicarboxylate is described.