293297-95-7

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester, (5S)-
• CAS NO: 293297-95-7
• Molecular Formula: C22H35NO4SeSi
• Molecular Weight: 484.57
• Mol File: 293297-95-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester, (5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester, (5S)-(293297-95-7)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester, (5S)-(293297-95-7)

Safety Data

• Hazardous Substances Data: 293297-95-7(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 126587-35-7 methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate 
• 45214-91-3 (2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98-79-3 L-Pyroglutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 
• 17342-08-4 (S)-Pyroglutaminol 
• 106191-02-0 (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one 
• 34837-55-3 Phenylselenyl bromide 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 5707-04-0 Phenylselenyl chloride 
• 96014-55-0 Methyl (4S)-4-(N-(tert-Butoxycarbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)pentanoate 
• 39538-20-0 (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 5-methyl ester 

Downstream Products

• 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 
• 1092504-90-9 N-({(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methyl)-1,3-benzoxazol-2-amine 
• 1092506-44-9 C₁₇H₁₉N₃OS 
• 1092506-43-8 {(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methanol 
• 1622235-69-1 (2S,3R)-3-(3-carboxy-5-hydroxyphenyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid 
• 1622235-85-1 (2S,3R)-3-(3-([1,1′-biphenyl]-3-ylmethoxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid 
• 1622154-08-8 (2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid 
• 1622235-84-0 (2S,3R)-1-(tert-butoxycarbonyl)-3-(3-carboxy-5-propoxyphenyl)-pyrrolidine-2-carboxylic acid 
• 1622235-81-7 (2S,3R)-tert-butyl 3-(3-([1,1′-biphenyl]-3-ylmethoxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)-pyrrolidine-1-carboxylate 
• 1622235-80-6 (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 1622235-79-3 (2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(3-(hydroxymethyl)-5-propoxyphenyl)pyrrolidine-1-carboxylate 
• 1622235-77-1 (2S,3R)-tert-butyl 3-(3-([1,1′-biphenyl]-3-ylmethoxy)-5-(((tertbutyldimethylsilyl)oxy)methyl)-phenyl)-2-(((tert-butyldimethylsilyl)-oxy)methyl)pyrrolidine-1-carboxylate 
• 1622235-76-0 (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate 
• 1622235-66-8 (2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)pyrrolidine-2-carboxylic acid hydrochloride 

Relevant articles and documents

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.

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.

Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N- boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones

We describe the photoinduced addition of methanol to 5(S)-5- triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-5- triisopropylsiloxymethyl-4(S)-hydroxymethyl-pyrrolidine-2-one, and conversion of this into a variety of 4(S), 5(S)-pyrrolidine-2-ones. Photo-induced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-(R)-N-boc-amino]ethyl- tetrahydrofuran-2-one via rearrangement of the initial photoadduct.