97538-67-5

Usage

Uses

Used in Pharmaceutical Development:
(2R,5S)-2-TRICHLOROMETHYL-3-OXA-1-AZABICYCLO[3.3.0]OCTAN-4-ONE is used as a reagent in organic synthesis for its potent bioactivity, particularly as an antimicrobial and antiviral agent. The trichloromethyl group in its structure is responsible for its strong biological properties, making it a valuable compound in the development of new pharmaceuticals.
Used in Research:
In the field of medicinal chemistry, (2R,5S)-2-TRICHLOROMETHYL-3-OXA-1-AZABICYCLO[3.3.0]OCTAN-4-ONE is used as a subject of study for its unique chemical structure and potential applications. Its versatility in organic synthesis and the possibility of exploring its properties for new therapeutic uses make it an important target for research.

InChI:InChI=1/C7H8Cl3NO2/c8-7(9,10)6-11-3-1-2-4(11)5(12)13-6/h4,6H,1-3H2/t4-,6+/m0/s1

Upstream product

• 302-17-0 chloral hydrate 
• 147-85-3 L-proline 
• 75-87-6 chloral 
• 515-83-3 chloral ethyl hemiacetal 

Downstream Products

• 29802-22-0 (S)-pyrrolidin-2-carboxylic acid dimethylamide 
• 850246-88-7 (S)-2-(methylaminocarbonyl)pyrrolidine-1-carbaldehyde 
• 121772-98-3 (R)-2-allylpyrrolidine-2-carboxylic acid 
• 76411-80-8 (S)-N-methyl-2-[(pyrrolidin-1-yl)methyl]pyrrolidine 
• 84466-85-3 (S)-1-methyl-2-(piperidinomethyl)pyrrolidine 
• 220060-08-2 methyl (S)-2-methylpyrrolidine-2-carboxylate monohydrochloride 
• 869001-98-9 dibenzyl N-benzyloxycarbonyl-glycyl-L-2-allylprolyl-L-glutamate 
• 915958-44-0 dibenzyl (2S,5'R)-2-[1'-(2''-benzyloxycarbonylamino-acetyl)-8'-hydroxy-6'-oxo-1',7'-diazaspiro[4.4]non-7'-yl]-pentanedioate 
• 869001-96-7 dibenzyl N-benzyloxycarbonyl-glycyl-L-2-ethylprolyl-L-glutamate 
• 869002-11-9 dibenzyl (2S,5'R)-2-[1'-(2''-benzyloxycarbonylamino-acetyl)-6'-oxo-1',7'-diazaspiro[4.4]non-7'-yl]-pentanedioate 
• 869002-01-7 di-tert-butyl N-tert-butyloxycarbonyl-glycyl-L-2-benzylprolyl-L-glutamate 
• 869001-88-7 N-benzyloxycarbonyl-glycyl-L-2-allylproline 
• 869001-92-3 N-tert-butyloxycarbonyl-glycyl-L-2-benzylproline 
• 869001-84-3 methyl N-tert-butyloxycarbonyl-glycyl-L-2-benzylprolinate 

Relevant academic research and scientific papers

Preparation method of N-phenylacetyl-2-hydroxymethylpyrrolidine-2-formamide and medicinal application of N-phenylacetyl-2-hydroxymethylpyrrolidine-2-formamide

The invention discloses N-phenylacetyl-2-hydroxymethylpyrrolidine-2-formamide as shown in a general formula (I), a preparation method of the compound, a new application of the compound and a pharmaceutical composition containing the compound in the aspect of inhibiting neuroglial cell inflammation. Wherein R1/R2 is equal to H, F, CF3 or OCF3.

Preparation method of (R)-1-alkanoyl-2-substituted pyrrolidine-2-formamide and medicinal application of (R)-1-alkanoyl-2-substituted pyrrolidine-2-formamide

The invention discloses (R)-1-alkanoyl-2-substituted pyrrolidine-2-formamide as shown in a general formula (I), a preparation method of a compound, a new application of the compound and a pharmaceutical composition containing the compound in the aspect of inhibiting neuroglial cell inflammation.

METHOD FOR PREPARATION OF ALPHA-METHYL-L-PROLINE

The invention discloses a method for preparation of alpha-methyl-L-proline starting from proline and comprising three steps, first a conversion with chloral, then a conversion with methyl bromide and then a conversion with aqueous HCl.

1,3-Oxazolidin-5-ones derived from proline as chiral components in the synthesis of predictive enantioselective coupling reagents

1,3-Oxazolidin-5-ones derived from both enantiomers of proline and trichloroacetaldehyde were prepared and applied as an amine component in the synthesis of chiral predictive triazine-based coupling reagents. The reagents were found to be useful in condensations yielding enantiomerically enriched products from racemic substrates.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed. Formula (I).

A Designed Approach to Enantiodivergent Enamine Catalysis

The rational design and implementation of enantiodivergent enamine catalysis is reported. A simple secondary amine catalyst, 2-methyl-l-proline, and its tetrabutylammonium salt function as an enantiodivergent catalyst pair delivering the enantiomers of α-functionalized aldehyde products in excellent enantioselectivities. This novel concept of designed enantiodivergence is applied to the enantioselective α-amination, aldol, and α-aminoxylation/α-hydroxyamination reactions of aldehydes.

A Convergent Synthesis of Enantiopure Open-Chain, Cyclic, and Fluorinated α-Amino Acids

A radical based synthesis of a broad variety of protected enantiopure α-amino acids, including fluorinated derivatives, is described. The radical addition furnishes naturally latent mercapto-α-amino acids ideally equipped for native chemical ligation.

STRUCTURAL MIMETICS OF PROLINE-RICH PEPTIDES AND USE THEREOF

The invention relates to compounds that can be used, in particular, as structural mimetics of proline-rich peptides and are correspondingly able to bond with proline-rich-motif binding domains (PRM domains) of proteins. The invention further relates to the use of these compounds as pharmaceutically active agents, as well as the use of the pharmaceutically active agents for the treatment of bacterial, neurodegenerative and tumor diseases.

Design and stereoselective synthesis of ProM-2: A spirocyclic diproline mimetic with polyproline type II (PPII) helix conformation

With the aim of developing polyproline type II helix (PPII) secondary-structure mimetics for the modulation of prolin-rich-mediated protein-protein interactions, the novel diproline mimetic ProM-2 was designed by bridging the two pyrrolidine rings of a diproline (Pro-Pro) unit through a Z-vinylidene moiety. This scaffold, which closely resembles a section of a PPII helix, was then stereoselectively synthesized by exploiting a ruthenium-catalyzed ring-closing metathesis (RCM) as a late key step. The required vinylproline building blocks, that is, (R)-N-Boc-2-vinylproline (Boc=tert-butyloxycarbonyl) and (S,S)-5-vinylproline-tert-butyl ester, were prepared on a gram scale as pure stereoisomers. The difficult peptide coupling of the sterically demanding building blocks was achieved in good yield and without epimerization by using 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU)/N,N-diisopropylethylamine (DIPEA). The RCM proceeded smoothly in the presence of the Grubbs II catalyst. Stereostructural assignments for several intermediates were secured by X-ray crystallography. As a proof of concept, it was shown that certain peptides containing ProM-2 exhibited improved (canonical) binding towards the Ena/VASP homology 1 (EVH1) domain as a relevant protein interaction target.