496841-09-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R)-methyl 3-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate is used as a key intermediate in the synthesis of pharmaceutical compounds for its unique structural features and potential to modulate biological activity.
Used in Organic Synthesis:
In the field of organic synthesis, (2S,3R)-methyl 3-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate serves as a versatile building block for creating a variety of complex organic molecules, leveraging its reactive functional groups and specific stereochemistry to form novel compounds with tailored properties.

InChI:InChI=1/C6H11NO3/c1-10-6(9)5-4(8)2-3-7-5/h4-5,7-8H,2-3H2,1H3/t4-,5+/m1/s1

Upstream product

• 1844898-16-3 (2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride 
• 496841-07-7 (2S,3R)-N-tert-Butyloxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic Acid Methyl Ester 
• 130966-46-0 (2S,3R)-N-tert-Butyloxycarbonyl-3-hydroxy-2-pyrrolidinecarboxylic Acid Methyl Ester 
• 76-05-1 trifluoroacetic acid 
• 217447-51-3 C₃₀H₄₄N₂O₉Si 
• 217447-49-9 Methyl (2R,3R)-5,5-dimethoxy-2-[N,N'-(dibenzylcarbonylhydrazino)]-3-hydroxypentanoate 
• 217447-41-1 methyl 5,5-dimethoxy-3-oxo-4-pentanoate 
• 217447-47-7 (R)-3-Hydroxy-5,5-dimethoxy-pentanoic acid methyl ester 
• 217447-52-4 (2R,3R)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethoxy-pentanoic acid methyl ester 
• 184046-78-4 (2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate 

Relevant academic research and scientific papers

Discovery of potent, orally-active, and muscle-selective androgen receptor modulators based on an N-aryl-hydroxybicyclohydantoin scaffold

A novel, N-aryl-bicyclohydantoin selective androgen receptor modulator scaffold was discovered through structure-guided modifications of androgen receptor antagonists. A prototype compound (7R,7aS)-10b from this series is a potent and highly tissue-selective agonist of the androgen receptor. After oral dosing in a rat atrophied levator ani muscle model, (7R,7aS)-10b demonstrated efficacy at restoring levator ani muscle mass to that of intact controls and exhibited >50-fold selectivity for muscle over prostate.

Intramolecular hydrogen bond-controlled prolyl amide isomerization in glucosyl 3′(S)-hydroxy-5′-hydroxymethylproline hybrids: Influence of a C-5′-hydroxymethyl substituent on the thermodynamics and kinetics of prolyl amide cis/trans isomerization

(Chemical Equation Presented) Peptide mimics containing spirocyclic glucosyl-(3′-hydroxy-5′-hydroxymethyl)proline hybrids (Glc3′(S)-5′(CH2OH)HypHs) with a polar hydroxymethyl substituent at the C-5′ position, such as C-terminal ester Ac-Glc3′(S

Synthesis and SAR of tetrahydropyrrolo[1,2-b][1,2,5]thiadiazol-2(3H)-one 1,1-dioxide analogues as highly potent selective androgen receptor modulators

Replacement of the 3-oxo group of 2-chloro-4-[(7R,7aS)-7-hydroxy-1,3-dioxotetrahydro-1H-pyrrolo[1,2c]imidazol-2(3H)-yl]-3-methylbenzonitrile resulted in a sulfamide series of selective androgen receptor modulator (SARM) agonists.

Rapid asymmetric synthesis of highly functionalized C5 chiral synthons. Practical preparation of trans-3 -hydroxy-D-proline

A stereocontrolled synthesis of (2R, 3R)-3-hydroxyproline 5 has been achieved in 33% overall yield from a prochiral β-ketoester : the methyl 5,5-dimethoxy-3-oxopentanoate 6. The key intermediate is the richly functionalized compound 4 which presented three different oxygenated groups and an anti relationship between the alcohol and the amine.