81658-27-7

Basic information

• Product Name: (2S,3R)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)diMethylsilyl-3,4-dehydro-pyroglutaMinol
• Synonyms: (2S,3R)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)diMethylsilyl-3,4-dehydro-pyroglutaMinol;1H-Pyrrole-1-carboxylic acid, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,5-dihydro-5-oxo-, 1,1-dimethylethyl ester, (2S)-
• CAS NO: 81658-27-7
• Molecular Formula: C₁₆H₂₉NO₄Si
• Molecular Weight: 327.49126
• Product Categories: Amines;Chiral Reagents;Heterocycles;Amines, Chiral Reagents, Heterocycles
• Mol File: 81658-27-7.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Ethyl Acetate
• CAS DataBase Reference: (2S,3R)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)diMethylsilyl-3,4-dehydro-pyroglutaMinol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)diMethylsilyl-3,4-dehydro-pyroglutaMinol(81658-27-7)
• EPA Substance Registry System: (2S,3R)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)diMethylsilyl-3,4-dehydro-pyroglutaMinol(81658-27-7)

Safety Data

• Hazardous Substances Data: 81658-27-7(Hazardous Substances Data)

Usage

Uses

Intermediate in the synthesis of (2S,3R)-3-Methylglutamic Acid, an agonist for kainate receptors.

Upstream product

• 888949-19-7 (5S)-N-tert-butoxycarbonyl-5-hydroxymethyl-1,5-dihydro-2H-pyrrol-2-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 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 
• 126587-35-7 methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate 
• 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 
• 81658-25-5 2-hydroxymethyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 141393-83-1 (4S,5S,6R)-N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-hept-2-enono-1,4-lactam 
• 141293-28-9 N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 246545-57-3 (-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-((1R)-hydroxyethyl)-5-oxopyrrolidine-1-carboxylate 
• 874454-29-2 (4R,5S)-1-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)-4-(4-(4-methoxybenzyloxy)but-1-en-2-yl)pyrrolidin-2-one 
• 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 
• 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 

Relevant articles and documents

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.

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.

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).