179990-59-1

Basic information

• Product Name: (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester
• Synonyms: (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester;(4R, 2S)-
• CAS NO: 179990-59-1
• Molecular Formula: C₂₅H₂₃NO₃
• Molecular Weight: 385.45502
• Product Categories: Aromatics;Heterocycles;Intermediates;Aromatics, Heterocycles, Intermediates
• Mol File: 179990-59-1.mol

Chemical Properties

• Melting Point: 63-66°C°C
• Boiling Point: 520.296°C at 760 mmHg
• Flash Point: 268.466°C
• Appearance: /
• Density: 1.289g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: Refrigerator
• Solubility: Chloroform
• CAS DataBase Reference: (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester(179990-59-1)
• EPA Substance Registry System: (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester(179990-59-1)

Safety Data

• Hazardous Substances Data: 179990-59-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester is used as a synthetic intermediate for the preparation of various complex organic molecules. Its unique structure allows it to serve as a building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. The chiral nature of (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester ensures that it can be used to create enantiomerically pure products, which is crucial for many applications in the chemical and pharmaceutical industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester is used as a key component in the development of new drugs. Its chiral center and specific functional groups make it a valuable candidate for the synthesis of biologically active molecules with potential therapeutic applications. (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester's ability to form stable intermediates in organic reactions also facilitates the creation of novel drug candidates with improved efficacy and selectivity.
Used in Research and Development:
(4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester is also utilized in academic and industrial research settings. It serves as a model compound for studying the reactivity and selectivity of various organic reactions, as well as the development of new synthetic methodologies. Researchers can use (4R, 2S)-4-Hydroxy-1-(9-phenyl-9H-fluoren-9-yl)-proline Methyl Ester to explore innovative approaches to asymmetric synthesis, catalysis, and other areas of organic chemistry.

InChI:InChI=1/C25H23NO3/c1-29-24(28)23-15-18(27)16-26(23)25(17-9-3-2-4-10-17)21-13-7-5-11-19(21)20-12-6-8-14-22(20)25/h2-14,18,23,27H,15-16H2,1H3/t18-,23+/m1/s1

Upstream product

• 55135-66-5 9-bromo-9-phenyl-9H-fluorene 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 160882-76-8 (2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 160882-76-8 (2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 255904-24-6 (2S,3S,1''R)-3-[1''-phenyl-1''-hydroxymethyl]-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 

Relevant articles and documents

Total synthesis of depsilairdin

(Figure presented) The total synthesis of depsilairdin, a host-selective phytotoxin isolated from Leptosphaeria maculans (the causal agent of blackleg disease of oilseed Brassicas), has been achieved by N-terminal extension of a suitably protected derivative of the hitherto unknown amino acid (2S,3S,4R)-3,4-dihydroxy-3-methyl-proline (Dhmp) followed by esterification with lairdinol A. The latter esterification, complicated by the sterically hindered nature of the carboxyl group, was accomplished by a novel method involving reaction of the 1-hydroxybenzotriazole (HOBt) derived active ester with the bromomagnesium alkoxide of lairdinol A. Three depsilairdin analogues were also prepared by replacing the Dhmp residue with l-proline and cis- and trans-4-hydroxy-l-proline. Phytotoxicity assays showed that the analogues were nontoxic to both blackleg-susceptible (brown mustard) and -resistant (canola) plants, suggesting that the presence of the Dhmp residue in depsilairdin is important for its host-selective toxicity toward brown mustard.

Enantiospecific and stereoselective synthesis of polyhydroxylated pyrrolidines and indolizidines from trans-4-hydroxy-L-proline

We have developed a short, efficient, and stereoselective synthesis of polyhydroxylated pyrrolidine and indolizidine glycosidase inhibitors starting from 4-hydroxy-L-proline. The regio- and stereoselective hydroxylation of an N-Pf-4-oxoproline enolate and the stereoselective reduction of the resulting keto alcohol allowed us to introduce the cis diol present in the target compounds. The different side chains needed to complete the syntheses of the target compounds were introduced by reduction of the ester group of a substituted proline or by reaction of organolithium or organomagnesium reagents with the same group followed by stereoselective reduction of the resulting ketones. Hydrogenolysis of the alcohols thus obtained gave the hydrochlorides of the desired pyrrolidine glycosidase inhibitors, which were obtained in nine steps in overall yields greater than 50%. The indolizidine glycosidase inhibitor 8-epi-swainsonine was also prepared using this approach.

Asymmetric Synthesis of 3S, 4R-Dihydroxypyrrolidines by Regio- and Stereoselective Hydroxylation of 4-Oxoproline Enolate

A short, efficient and stereoselective synthesis of enantiomerically pure (2R,3S,4R) 3,4-dihydroxy-2-hydroxymethylpyrrolidine, a galactosidase inhibitor, from 4-hydroxy-L-proline is presented.The key steps are the regio- and stereoselective hydroxylation