62592-80-7

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-5-Hydroxy-2-pentenoic Acid Methyl Ester is used as an intermediate in the synthesis of unusual amino acids for their potential as Michael acceptor-based antiplasmodial and antitrypanosomal cysteine protease inhibitors. These inhibitors play a significant role in the development of new therapeutic strategies against parasitic diseases, particularly malaria and trypanosomiasis, by targeting essential proteases in the parasites' life cycle.

InChI:InChI=1/C6H10O3/c1-9-6(8)4-2-3-5-7/h2,4,7H,3,5H2,1H3

Upstream product

• 688801-64-1 (E)-methyl 5-[(tert-butyldimethylsilyl)oxy]pent-2-enoate 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 
• 504-63-2 trimethyleneglycol 
• 201667-72-3 methyl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate 

Downstream Products

• 876392-17-5 4-(N-(p-toluenesulfonyl)-3-methylene-2,3-dihydroindol-2-yl)butanal 
• 894810-73-2 N-(4-(methoxycarbonyl)-1-butenyl)-N-(p-toluenesulfonyl)-2-ethenylaniline 
• 876392-15-3 N-(p-toluenesulfonyl)-2-(3-(methoxycarbonyl)propyl)-3-methylene-2,3-dihydroindole 
• 894810-76-5 3-methylene-2-pent-4-enyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole 
• 123282-88-2 methyl (E)-5-bromo-2-pentenoate 
• 876392-11-9 N-(4-(methoxycarbonyl)-3-butenyl)-N-(p-toluenesulfonyl)-2-ethenylaniline 
• 62592-76-1 methyl (E)-5-mesyloxypentan-2-enoate 

Relevant academic research and scientific papers

Synthesis of Highly Functionalized Hydrindanes via Sequential Organocatalytic Michael/Mukaiyama Aldol Addition and Telescoped Hydrozirconation/Cross-Coupling as Key Steps: En Route to the AB System of Clifednamides

The AB ring systems of the clifednamide family, polycyclic tetramate macrolactames (PoTeMs), were prepared by a new, convergent approach employing an intramolecular Diels-Alder (IMDA) reaction. Key steps comprise an organocatalytic Michael addition (>90% enantiomeric excess (ee)), a Mukaiyama aldol reaction for the convergent installation of a diene moiety, and a telescoped hydrozirconation/cross-coupling grafting an enone. The following IMDA furnished a highly functionalized hydrindane (diastereomeric ratio (dr) = 91:1) with the same configuration as the clifednamide scaffold. Advantages of this route are only one required protecting group, 13% overall yield over 9 steps (reduced from previously 17 steps/1.3% overall), and the potential access to the key intermediates in the clifednamide biosynthesis.

Synthesis of (±)-oleocanthal via a tandem intramolecular Michael cyclization-HWE olefination

A synthesis of racemic oleocanthal has been accomplished in 11 steps from 1,3 propanediol by a key tandem intramolecular Michael cyclization-Horner-Wadsworth-Emmons olefination.

Stereodivergent approach to enantiopure hydroxyindolizidines through 1,3-dipolar cycloaddition of 3-hydroxypyrroline N-oxide derivatives

The (3S)-3-alkoxypyrroline N-oxides 7 and 27 were easily prepared from 1-malic acid and used as starting materials for enantiospecific syntheses of stereo differentiated polyhydro-xyindolizidines. Selection of the appropriate modality (inter or intramolec