220993-22-6

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester is used as a key intermediate in the synthesis of oxazolidinone derivatives, which are a class of antibiotics with potent antibacterial activity. These derivatives are effective against a wide range of gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester's unique structure allows for the development of new antibiotics with improved properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Antibacterial Applications:
(2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester is used as a precursor for the preparation of antibacterial oxazolidinone derivatives. These derivatives exhibit broad-spectrum antibacterial activity and are particularly useful in treating infections caused by drug-resistant bacteria. (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester's role in the synthesis of these derivatives is crucial for the development of new and effective antibacterial agents to combat the growing threat of antibiotic resistance.

Upstream product

• 125653-58-9 (2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 51-35-4 4R-4-hydroxyproline 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 

Downstream Products

• 540501-65-3 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine 
• 540501-23-3 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-methylenepyrrolidine 
• 540501-26-6 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine 
• 540501-28-8 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(4'-ethoxyphenyl)methylenepyrrolidine 
• 540501-44-8 (2S,4R)-N-tert-butyloxycarbonyl-4-(4'-ethoxy)benzyl-2-hydroxymethylpyrrolidine 
• 540501-39-1 (S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 83623-78-3 (2S,4S)-4-benzyl-N-tert-butyloxycarbonylproline 
• 153074-95-4 (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 540501-64-2 (2S,4R)-N-tert-butyloxycarbonyl-4-(methoxycarbonyl)methylproline 
• 540501-64-2 (2S,4S)-N-tert-butyloxycarbonyl-4-(methoxycarbonyl)methylproline 
• 540501-37-9 (S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 540501-43-7 (2S,4R)-N-tert-butyloxycarbonyl-4-benzyl-2-hydroxymethylpyrrolidine 
• 540501-62-0 (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline 
• 540501-47-1 (2S,4R)-N-tert-butyloxycarbonyl-4-propylproline 

Relevant academic research and scientific papers

Design, Synthesis, and Pharmacological Evaluation of Potent Positive Allosteric Modulators of the Glucagon-like Peptide-1 Receptor (GLP-1R)

The therapeutic success of peptidic GLP-1 receptor agonists for treatment of type 2 diabetes mellitus (T2DM) motivated our search for orally bioavailable small molecules that can activate the GLP-1 receptor (GLP-1R) as a well-validated target for T2DM. Here, the discovery and characterization of a potent and selective positive allosteric modulator (PAM) for GLP-1R based on a 3,4,5,6-tetrahydro-1H-1,5-epiminoazocino[4,5-b]indole scaffold is reported. Optimization of this series from HTS was supported by a GLP-1R ligand binding model. Biological in vitro testing revealed favorable ADME and pharmacological profiles for the best compound 19. Characterization by in vivo pharmacokinetic and pharmacological studies demonstrated that 19 activates GLP-1R as positive allosteric modulator (PAM) in the presence of the much less active endogenous degradation product GLP1(9-36)NH2 of the potent endogenous ligand GLP-1(7-36)NH2. While these data suggest the potential of small molecule GLP-1R PAMs for T2DM treatment, further optimization is still required towards a clinical candidate.

PYRROLOBENZODIAZEPINE DIMER PRECURSOR AND LIGAND-LINKER CONJUGATE COMPOUND THEREOF

The present invention relates to a pyrrolobenzodiazepine dimer prodrug and a ligand-linker conjugate compound thereof, a composition containing these, and therapeutic use thereof particularly as an anticancer drug. The stability of the compounds themselves and the stability thereof in plasma are excellent and the compounds are advantageous in terms of manifestation of toxicity, and thus the compounds are industrially useful in that it is possible to target proliferative diseases such as cancer, to perform a specific treatment, to maximize the drug efficacy, and to minimize the occurrence of side effects.

Asymmetric hydrogenations for the synthesis of boc-protected 4-alkylprolinols and prolines

The utility of 4-substituted prolinols and their corresponding prolines in peptides, peptidomimetics, and natural products has motivated researchers to find new and efficient routes for their preparation. Herein, we report a general approach to the synthesis of Boc-protected 4-alkylprolinols and prolines via a divergent asymmetric hydrogenation strategy. Intermediate exocyclic olefins were prepared by Wittig-type reactions with ketone 6 and subjected to hydroxyl and sterically directed reductions. The Crabtree catalyst (Ir[COD] PyPCy3PF6) proved to be highly effective in diastereoselective hydrogenations to give trans- substituted pyrrolidines (9). Good facial selectivities were also observed in heterogeneous hydrogenations with Raney-nickel to obtain cis-substituted pyrrolidines (11). Employing this strategy, we describe the synthesis of novel prolinol and proline-based building blocks for incorporation into biologically relevant peptidomimetics.

Antibiotic oxazolidinone derivatives

The invention concerns a compound of the formula (I): wherein, for example:T is of the formula (IA), (IB), or (IC); R1 is of the formula —NHC(=O)Rb wherein Rb is (1-4C)alkyl;R2 and R3 are hydrogen or