913820-71-0

Basic information

• Product Name: (4R)-4-Fluoro-D-proline
• Synonyms: (4R)-4-Fluoro-D-proline
• CAS NO: 913820-71-0
• Molecular Formula: C5H8FNO2
• Molecular Weight: 133.1209232
• Mol File: 913820-71-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4R)-4-Fluoro-D-proline(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-Fluoro-D-proline(913820-71-0)
• EPA Substance Registry System: (4R)-4-Fluoro-D-proline(913820-71-0)

Safety Data

• Hazardous Substances Data: 913820-71-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(4R)-4-Fluoro-D-proline is utilized as a building block in the synthesis of novel therapeutic agents, due to its unique structural properties that can influence the conformation and function of proteins. It is particularly valuable in the design of drugs targeting specific protein interactions, offering a means to modulate biological activity through structural modifications.
Used in Medicinal Chemistry:
(4R)-4-Fluoro-D-proline serves as a key component in the exploration of new chemical entities and the study of protein structure modifications. Its chirality and fluorination provide a basis for investigating the effects of stereochemistry and functional group substitution on biological activity, which is crucial for optimizing drug efficacy and selectivity.
Used in Protein Engineering:
As a modified amino acid, (4R)-4-Fluoro-D-proline is employed in protein engineering to create proteins with altered properties. This can lead to the development of proteins with improved stability, specificity, or activity, which may have applications in various therapeutic areas, including enzyme replacement therapies and targeted drug delivery systems.
Used in Biochemical Studies:
(4R)-4-Fluoro-D-proline is applied in biochemical research to probe the role of proline in protein folding, stability, and function. Its incorporation into peptides and proteins allows scientists to study the effects of proline substitution on protein conformation and dynamics, providing insights into the fundamental mechanisms of protein behavior and its implications for drug design.

Upstream product

• 203866-13-1 (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid 
• 132651-95-7 Methyl 1-acetyl-4-fluoro-D-prolinate 
• 203866-14-2 (2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid 
• 203866-18-6 methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate 
• 129430-93-9 (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 129430-93-9 methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 618-27-9 hydroxy L-proline 
• 148429-59-8 (6S,7aS)-6-hydroxy-3,3-bis(trifluoromethyl)tetrahydro-pyrrolo[1,2-c]oxazol-1-one 
• 156046-04-7 (5S,7R)-7-fluoro-2,2-bis(trifluoromethyl)-1-aza-3-oxabicyclo<3.3.0>octan-4-one 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 203866-16-4 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 231282-75-0 (6R,7aS)-6-hydroxy-3,3-bis(trifluoromethyl)tetrahydro-pyrrolo[1,2-c]oxazol-1-one 

Downstream Products

• 79108-50-2 1-Nitroso-cis-4-fluoro-L-proline 
• 203866-19-7 (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid 
• 587888-04-8 N-tert-butoxycarbonyl-(2S,4S)-4-fluoroproline benzyl ester 
• 1612854-12-2 C₅₃H₆₂F₂N₈O₇ 
• 1612854-09-7 C₁₉H₂₄BrFN₄O₅ 

Relevant articles and documents

HETEROCYCLYL SUBSTITUTED PYRROLOPYRIDINES THAT ARE INHIBITORS OF THE CDK12 KINASE

This invention relates to compounds that are inhibitors of the CDK12 kinase. The compounds are useful in the treatment of disorders mediated by CDK12 kinase including myotonic dystrophy type 1 (DM1) and other disorders caused by the generation of RNA repeat expansion transcripts. In particular,the invention relates to compounds of the formula (I), or a pharmaceutically acceptable salts or N-oxides thereof, wherein R1a, R2, R3, R4a, R4b and R4c are as defined herein.

SPIRO RING COMPOUND AS HEPATITIS C VIRUS (HCV) INHIBITOR AND USES THEREOF FIELD OF THE INVENTION

A compound of formula (I) or a stereoisomer, a geometric isomer. a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof is provided, which can be used for treating HCV infection or a HCV disorder. Also a pharmaceutical composition comprising the compound and the use of the compound and the pharmaceutical composition thereof are provided, which can also be used for treating HCV infection or a HCV disorder.

Fluorous synthesis of 18F radiotracers with the [ 18F]fluoride ion: Nucleophilic fluorination as the detagging process

Tag team: The flouro-detagging of flourous sulfonates by the [ 18F]fluoride ion was found to be an advantageous strategy for the preparation of various 18F-labeled prosthetic groups and known radiotracers (see picture). Fluorous solid phase extraction (FSPE) was used to separate the excess fluorous precursor from the labeled material, which suggests that traditional purification protocols such as distillation or tedious separation can be avoided. (Chemical Equation Presented).

N-arylsulfonamide- and pyrrolidinecarboxylic acid intermediates, and their use for the preparation of herbicidal 1,3-dioxo-1h-pyrrolo[1,2-c]imidazole derivatives

This invention is directed to compounds and intermediates of Formulae 6 and 3, useful in preparing herbicidal sulfonamides of Formula 1, including all geometric and stereoisomers thereof, and agricultural salts thereof. wherein the substituents are define

Synthesis of n.c.a. cis- and trans-4-[18F]fluoro-L-proline, radiotracers for PET-investigation of disordered matrix protein synthesis

A radiosynthesis of n.c.a. (2S,4R)-4-[18F]fluoroproline (trans-configuration) and its diastereomer (2S,4S)-4-[18F]fluoroproline (cis-configuration) has been developed. It allows the routine production of up to 18 GBq of product for c

Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline

Boc-cis-4-fluoro-L-proline and 4-difluoro-L-proline, usable in classical peptide synthesis, were obtained in respectively 71% (3 steps) and 65% (4 steps) overall yields from the readily available trans-4-hydroxy-L-proline methyl ester. The corresponding fluorinated trans-isomer was isolated in 24% yield (5 steps). Transformation of Boc-protected compounds to their Fmoc-equivalents was performed in high yields.

Synthesis of (2S)-4,4-difluoroproline, (2S,4R)-4-fluoroproline and their derivatives from (S)-aspartic acid

Syntheses for (2S)-4,4-difluoroproline, (2S,4R)-4-fluoroproline and their derivatives are described starting from (S)-aspartic acid, using hexafluoroacetone as the protecting reagent and DAST as the fluorinating agent.

Stereospecific syntheses of all four stereoisomers of 4-fluoroglutamic acid

(+)-L-threo-4-fluoroglutamic acid . (-)-D-threo-4-Fluoroglutamic acid was prepared analogously from trans-4-hydroxy-D-proline, obtained from its diastereomer by inversion of configuration at carbon 4 of the pyrrolidine ring using the diethyl azodicarboxylate-triphenylphosphine procedure. cis-4-Hydroxy-L-proline, necessary for the synthesis of (+)-L-erythro-4-fluoroglutamic acid , was prepared from trans-4-hydroxy-L-proline by benzyloxycarbonylation at the nitrogen, oxidation of the 1-benzyloxycarbonyl-trans-4-hydroxy-L-proline to 1-benzyloxycarbonyl-4-oxo-L-proline, its reduction to 1-benzyloxycarbonyl-cis-4-hydroxy-L-proline and deprotection of the latter at the nitrogen. (-)-cis-4-Fluoro-L-proline and (+)-trans-4-fluoro-D-proline were isolated after the hydrolysis of incompletely oxidized methyl 1-acetyl-cis-4-fluoro-L-prolinate and methyl 1-acetyl-trans-4-fluoro-D-prolinate, respectively.