81658-26-6

Basic information

• Product Name: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINECARBOXYLATE-1,1-DIMETHYLETHYL ESTER
• Synonyms: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINECARBOXYLATE-1,1-DIMETHYLETHYL ESTER;L-1-BOC-O-TBDMS-PYROGLUTAMINOL;(2S,3R)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)diMethylsilyl-pyroglutaMinol;(2S)-N-(tert-Butyloxycarbonyl)-O-(tert-butyl)diMethylsilyl-pyroglutaMinol;1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-5-oxo-, 1,1-dimethylethyl ester, (S)-;(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate
• CAS NO: 81658-26-6
• Molecular Formula: C₁₆H₃₁NO₄Si
• Molecular Weight: 329.51
• Product Categories: Amines;Chiral Reagents;Heterocycles;Amines, Chiral Reagents, Heterocycles
• Mol File: 81658-26-6.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Dichloromethane
• CAS DataBase Reference: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINECARBOXYLATE-1,1-DIMETHYLETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINECARBOXYLATE-1,1-DIMETHYLETHYL ESTER(81658-26-6)
• EPA Substance Registry System: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINECARBOXYLATE-1,1-DIMETHYLETHYL ESTER(81658-26-6)

Safety Data

• Hazardous Substances Data: 81658-26-6(Hazardous Substances Data)

Usage

Uses

Protected (S)-Pyroglutaminol (P997525). Intermediate in the synthesis of (2S,3R)-3-Methylglutamic Acid, an agonist for kainate receptors.

Upstream product

• 81658-27-7 (S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 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 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 141393-83-1 (4S,5S,6R)-N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-hept-2-enono-1,4-lactam 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 185303-86-0 N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-L-arabinoheptono-1,4-lactam 
• 141393-87-5 4-<(tert-butoxycarbonyl)amino>-6,7-O-isopropylidene-2,3,4-trideoxy-L-arabino-hept-2-enonic acid 1,4-lactam 
• 185303-87-1 tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate 

Downstream Products

• 108732-21-4 (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-(tert-butyldimethylsilyl)oxymethyl-5-pyrrolidone 
• 81658-25-5 2-hydroxymethyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 364343-08-8 C₂₂⁽¹³⁾CH₃₇NO₄SeSi 
• 145221-00-7 (S)-5-Methoxymethyl-2-oxo-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 376586-88-8 3-benzyloxycarbonyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 293297-95-7 (5S)-N-(tert-Butoxycarbonyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(phenylseleno)pyrrolidin-2-one 
• 129413-76-9 (3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 129413-78-1 5(S)-((t-butyl-dimethyl-silyloxy)methyl)-3(R)-phenylmethyl-N-BOC-2-pyrrolidinone 
• 129413-77-0 (3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-5-phenyl-pent-2-enyl)-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 
• 1463501-50-9 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde 

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.

A cascade strategy enables a total synthesis of (-)-gephyrotoxin

A concise and efficient synthesis of (-)-gephyro-toxinfrom L-pyroglutaminol has been realized. The key step in this approach is a diastereoselective intramolecular enamine/ Michael cascade reaction that forms two rings and two stereocenters and generates a stable tricyclic iminium cation. A hydroxy-directed reduction of this intermediate plays a key role in establishing the required cis-decahydroquinoline ring system, enabling the total synthesis of (-)-gephyrotoxin in nine steps and 14 % overall yield. The absolute configuration of the synthetic material was confirmed by single-crystal X-ray diffraction and is consistent with the structure originally proposed for material isolated from the natural source.