99208-71-6

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3,3-DiMethyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one is utilized as a potential active pharmaceutical ingredient for the development of new drugs. Its chiral nature and heterocyclic structure may contribute to its interaction with biological targets, offering therapeutic benefits in various medical conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (S)-3,3-DiMethyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one serves as a valuable compound for studying its structural and stereochemical properties. This research can lead to a better understanding of its potential biological activities and inform the design of more effective and selective drugs.

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 17342-08-4 (S)-Pyroglutaminol 
• 116-11-0 2-Methoxypropene 
• 98-79-3 L-Pyroglutamic acid 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 4931-66-2 methyl (S)-pyroglutamate 

Downstream Products

• 627503-43-9 (S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one 
• 627503-45-1 (S)-3,3-bis(2,4,6-triisopropylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one 
• 950172-17-5 (5S)-1-aza-2,2-dimethyl-7,7-di(p-chlorobenzyl)-3-oxa-8-oxo-bicyclo[3.3.0]octane 
• 950172-16-4 (5S)-1-aza-2,2-dimethyl-7,7-di(p-fluorobenzyl)-3-oxa-8-oxo-bicyclo[3.3.0]octane 
• 212890-88-5 (S)-(+)-1-aza-3,3-bisbenzyl-8,8-dimethyl-7-oxabicyclo[3.3.0]octan-2-one 
• 950172-18-6 (5S)-1-aza-2,2-dimethyl-7,7-di(p-methoxybenzyl)-3-oxa-8-oxo-bicyclo[3.3.0]octane 
• 212890-90-9 (S)-(+)-(4,4-dibenzylpyrrolidin-2-yl)methan-1-ol 
• 212890-91-0 (S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate 
• 212890-92-1 (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate 
• 212890-93-2 (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[(diphenylphosphino)methyl]pyrrolidinecarboxylate 
• 156088-48-1 (5S)-1-(2,2-dimethylpropionyl)-3,3-dimethyl-5-trityloxymethylpyrrolidin-2-one 
• 1817630-30-0 (3S,4S,5S)-4-ethyl-3-fluoro-5-(hydroxymethyl)-pyrrolidin-2-one 
• 1263285-61-5 (1S,4S,5R)-4-(hydroxymethyl)-3-azabicyclo[3.1.0]hexan-2-one 
• 1817626-54-2 PF-06650833 

Relevant academic research and scientific papers

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same. The compounds include an IRAK binding moiety and a degradation inducing moiety (DIM). The DIM could be DTM a ligase binding moiety (LBM) or lysine mimetic. The compounds could be useful as IRAK protein kinase inhibitors and applied to IRAK mediated disorders.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Synthetic studies towards the core structure of nakadomarin a by a thioamide-based strategy

The tricyclic BCD substructure of the marine natural product nakadomarin A has been synthesised. The strategy utilised a key carbon-carbon bond-forming reaction between a furan and an N-acyliminium ion derived from a secondary thiolactam. In addition, a novel three-component coupling reaction between a thioamide, an allylic bromide and an isocyanate, leading to the establishment of two new stereogenic centres, is reported. Two key steps in a projected total synthesis of nakadomarin A have been realised by using the unique chemistry of thioamides. Formation of the carbocyclic B ring can be effected by nucleophilic attack of a furan on a thiolactam-derived iminium ion, and the key quaternary centre can be established by a novel three-component coupling reaction.

SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS

The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R1, R2, R4, R3, R5 and R6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2′,3′-dideoxy-2′,2′-difluoro-4′-azanucleosides

A series of 2′,3′-dideoxy-2′,2′-difluoro-4′- azanucleosides of both pyrimidine and purine nucleobases were synthesized in an efficient manner starting from commercially available L-pyroglutamic acid via glycosylation of difluorinated pyrrolidine derivative 15. Several 4′-azanucleosides were prepared as a separable mixture of α- and β-anomers. The 6-chloropurine analogue was obtained as a mixture of N 7 and N9 regioisomers and their structures were identified based on NOESY and HMBC spectral data. Among the 4′-azanucleosides tested as HIV-1 inhibitors in primary human lymphocytes, four compounds showed modest activity and the 5-fluorouracil analogue (18d) was found to be the most active compound (EC50 = 36.9 μM) in this series. None of the compounds synthesized in this study demonstrated anti-HCV activity.

SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS

The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R1, R2, R4, R3, R5 and R6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

Synthesis and utility of the 3,3-dimethyl-5-substituted-2-pyrrolidinone 'Quat' chiral auxiliary

The synthesis and utility of the 3,3-dimethyl-5-substituted-2-pyrrolidinone 'Quat' chiral auxiliary in stereoselective enolate reactions of attached N-acyl side chains combined with the mild and non-racemising conditions required for the ultimate removal of the chiral side chain is described.

Electrophilic fluorination of pyroglutamic acid derivatives: Application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids

Electrophilic fluorination of enantiomerically pure 2-pyrrolidinones (4) derived from (L)-glutamic acid has been investigated as a method for the synthesis of single stereoisomers of 4-fluorinated glutamic acids. Reaction of the lactam enolate derived from 9 with NFSi results in a completely diastereoselective monofluorination reaction to yield the monocyclic trans-substituted α-fluoro lactam product 21. Unfortunately, a decreased kinetic acidity in 21 and other structurally related monofluorinated products renders them resistant to a second fluorination. In contrast, the bicyclic lactam 12 is readily difluorinated under the standard conditions described to yield the α,α-difluoro lactam 24. The difference in reactivity between the two types of related lactams is attributed mainly to the presence or lack of a steric interaction between the base used for deprotonation and the protecting group present in the pyrrolidinone substrates. This conclusion was reached based on analysis of the X-ray crystal structure of 21, molecular modeling, and experimental evidence. The key intermediates 21 and 24 are converted to (2S,4R)-4-fluoroglutamic acid and (2S)-4,4-difluoroglutamic acid, respectively.

Synthesis of L-4,4-difluoroglutamic acid via electrophilic difluorination of a lactam.

[formula: see text] An enantiomerically pure bicyclic lactam proved to be an excellent substrate for electrophilic difluorination using N-fluorobenzenesulfonimide. The resulting difluorinated lactam can be easily converted into L-4,4-difluoroglutamic acid. To the best of our knowledge, this is the first example of a synthetically useful electrophilic difluorination of an unactivated lactam.