81658-27-7

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)diMethylsilyl-3,4-dehydro-pyroglutaMinol is used as an intermediate in the synthesis of (2S,3R)-3-Methylglutamic Acid for its agonistic properties towards kainate receptors. This makes it a valuable component in the development of pharmaceuticals targeting neurological conditions and disorders related to the function of these receptors.

Upstream product

• 293297-95-7 (5S)-N-(tert-Butoxycarbonyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(phenylseleno)pyrrolidin-2-one 
• 888949-19-7 (5S)-N-tert-butoxycarbonyl-5-hydroxymethyl-1,5-dihydro-2H-pyrrol-2-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 138871-58-6 (S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 56-86-0 L-glutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 141293-28-9 N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 
• 126587-35-7 methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate 
• 39538-20-0 (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 5-methyl ester 
• 96014-55-0 Methyl (4S)-4-(N-(tert-Butoxycarbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)pentanoate 
• 45214-91-3 (2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid 
• 53100-44-0 L-N-t-butoxycarbonylpyroglutamic acid 
• 185303-87-1 tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate 

Downstream Products

• 126587-42-6 (2S,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-oxo-3-(phenyl-phenylsulfanyl-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 210534-34-2 (2S,3R)-3-(4-Bromo-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 210534-17-1 (4R,5S)-1-tert-butoxycarbonyl-(5-tert-butyldimethylsilyloxymethyl)-4-phenylpyrrolidin-2-one 
• 220623-07-4 (1S,2S,5R)-tert-butyl 3-aza-4-oxo-2-<(1,1,2,2-tetramethyl-1-silapropoxy)methyl>bicyclo<3.1.0>hexane-3-carboxylate 
• 246545-57-3 (-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-((1R)-hydroxyethyl)-5-oxopyrrolidine-1-carboxylate 
• 246545-53-9 (+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate 
• 348642-87-5 3-[4-benzyloxy-2-(1,2-dimethyl-propenyl)-phenyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 126587-43-7 (2S,3S)-3-benzyl-1-<(1,1-dimethylethoxy)carbonyl>-2-<<(1,1-dimethylethyl)dimethylsilyloxy>methyl>-5-pyrrolidone 
• 855517-77-0 (2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 874454-29-2 (4R,5S)-1-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)-4-(4-(4-methoxybenzyloxy)but-1-en-2-yl)pyrrolidin-2-one 
• 745014-14-6 (4R,5S)-5-Hydroxymethyl-4-isopropyl-pyrrolidin-2-one 
• 696645-92-8 ((2S,3S)-3-Benzyl-pyrrolidin-2-yl)-methanol 
• 745014-67-9 (4S,5S)-4-Benzyl-5-hydroxymethyl-pyrrolidin-2-one 

Relevant academic research and scientific papers

Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin

The Pt-catalyzed diboration of cyclic alkenes is extended to unsaturated heterocycles and bicyclic compounds and can be accomplished in a diastereoselective fashion. The optimal procedures, substrate scope, and diastereoselectivity were investigated, and examples employing both homogeneous and heterogeneous catalysis were examined. Lastly, application to the construction of the nucleoside analog (±)-aristeromycin was conducted.

Structure-Activity Relationship Study of Ionotropic Glutamate Receptor Antagonist (2S,3R)-3-(3-Carboxyphenyl)pyrrolidine-2-carboxylic Acid

Herein we describe the first structure-activity relationship study of the broad-range iGluR antagonist (2S,3R)-3-(3-carboxyphenyl)pyrrolidine-2-carboxylic acid (1) by exploring the pharmacological effect of substituents in the 4, 4′, or 5′ positions and the bioisosteric substitution of the distal carboxylic acid for a phosphonic acid moiety. Of particular interest is a hydroxyl group in the 4′ position 2a which induced a preference in binding affinity for homomeric GluK3 over GluK1 (Ki = 0.87 and 4.8 μM, respectively). Two X-ray structures of ligand binding domains were obtained: 2e in GluA2-LBD and 2f in GluK1-LBD, both at 1.9 ? resolution. Compound 2e induces a D1-D2 domain opening in GluA2-LBD of 17.3-18.8° and 2f a domain opening in GluK1-LBD of 17.0-17.5° relative to the structures with glutamate. The pyrrolidine-2-carboxylate moiety of 2e and 2f shows a similar binding mode as kainate. The 3-carboxyphenyl ring of 2e and 2f forms contacts comparable to those of the distal carboxylate in kainate.

PYRROLIDINE-2-CARBOXYLIC ACID DERIVATIVES AS IGLUR ANTAGONISTS

The present invention relates to compounds of Formula (I), combinations and use thereof for disease therapy, or pharmaceutically acceptable salt or solvate thereof, including all tautomers, stereoismers and polymorphs thereof, which are iGluR receptor inhibitors, and hence are useful in the treatment of psychiatric diseases or neurological disorders or a disease or disorder associated with abnormal activities of iGluR receptors.

PYRROLIDINE-2-CARBOXYLIC ACID DERIVATIVES AS IGLUR ANTAGONISTS

The present invention relates to compounds of Formula (I), combinations and use thereof for disease therapy, or pharmaceutically acceptable salt or solvate thereof, including all tautomers, stereoismers and polymorphs thereof, which are iGlu R inhibitors, and hence are useful in the treatment of psychiatric diseases or neurological disorders or a disease or disorder associated with abnormal activities of iGluR receptors.

Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors

In this paper we describe the rational design, synthesis and pharmacological evaluation of two new stereoisomeric (S)-glutamate (Glu) analogues. The rational design was based on hybrid structures of the natural product kainic acid, a synthetic analogue CPAA and the high-affinity Glu analogue SYM2081. Pharmacological evaluation of the two stereoisomers revealed that one stereoisomer showed a subtype selectivity profile with low micromolar affinity for GluK1 and GluK3 and a 10- to 15-fold lower affinity for GluK2. The other stereoisomer displayed full selectivity for the KA over AMPA and NMDA receptors (GluK1-3: 0.39, 0.51 and 0.099μM, respectively).

CYCLOPROPYL PYRROLIDINE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to cyclopropyl proline bis-amide compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which orexin receptors are involved.

Functionalized pyrrolidine inhibitors of human type II α-mannosidases as anti-cancer agents: Optimizing the fit to the active site

Refining the chemical structure of functionalized pyrrolidine-based inhibitors of Golgi α-mannosidase II (GMII) to optimize binding affinity provided a lead molecule that demonstrated nanomolar competitive inhibition of α-mannosidases II and an optimal fit in the active site of Drosophila GMII by X-ray crystallography. Esters of this lead compound also inhibited the growth of human glioblastoma and brain-derived endothelial cells more than the growth of non-tumoral human fibroblasts, suggesting their potential for anti-cancer therapy.

Investigation of a route to ibotenic acid analogues via a reduced pyroglutamate template

Two alternative "ring switch" based syntheses have been shown to give access to the reduced protected homochiral analogues, 27, 28 and 36, of the CNS active compound ibotenic acid. The Royal Society of Chemistry 2006.

A facile entry to bicyclic systems from L-glutamic acid

An efficient synthesis of bicyclic heterocycles has been realized from L-glutamic acid. The key step is the construction of the pyrrole ring in a single step, using tosylmethyl isocyanide (TosMIC) methodology. Structures of reaction intermediates and final products were investigated using density functional theory calculations.

Synthesis and analysis of the sterically constrained L-glutamine analogues (3S,4R)-3,4-dimethyl-L-glutamine and (3S,4R)-3,4-dimethyl-L-pyroglutamic acid

The nonproteinogenic amino acids (3S,4R)-3,4-dimethyl-L-pyroglutamic acid and (3S,4R)-3,4-dimethyl-L-glutamine - found in the cyclic depsipeptides callipeltin B, callipeltin A, and papuamide A - were synthesized from a common intermediate derived from L-pyroglutamic acid. The diastereoselective introduction of the methyl groups was accomplished by cuprate addition and enolate alkylation, followed by a kinetic epimerization of the C-4 methyl substituent. (3S,4R)-3,4-Dimethyl-L-glutamine shows a conformational restriction of its side chain which may be related to its biological function in the natural products where it is found.