114676-59-4

Basic information

• Product Name: D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)-
• Synonyms: D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)-;Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride;(2R,4R)-4-Hydroxy-2-(methoxycarbonyl)pyrrolidine hydrochloride, cis-4-Hydroxy-D-proline methyl ester hydrochloride;Methyl 4-hydroxypyrrolidine-2-carboxylate HCl;D-Proline, 4-hydroxy-, Methyl ester, hydrochloride, (4R)-;Cis-4-Hydroxy-D-proline Methyl ester HCl;(2R,4R)-4-Hydroxypyrrolidine-2-carboxylic acid methyl ester hydrochloride;Cis-4-hydroxy-proline Methyl ester hydrochloride -D-
• CAS NO: 114676-59-4
• Molecular Formula: C₆H₁₁NO₃*ClH
• Molecular Weight: 181.618
• Mol File: 114676-59-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: 121-123℃
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)-(114676-59-4)
• EPA Substance Registry System: D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)-(114676-59-4)

Safety Data

• Hazardous Substances Data: 114676-59-4(Hazardous Substances Data)

Usage

General Description

D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)- is a chemical compound that is a derivative of the amino acid proline. It is commonly used in organic synthesis and as a biochemical research reagent. The compound is a hydrochloride salt, and its 4R configuration indicates that it is the enantiomer of proline with a specific spatial arrangement of atoms. It has potential applications in pharmaceuticals and drug development, as well as in the production of specialized chemicals and materials. The compound may also have biological activities and functions that could be of interest for further study.

Upstream product

• 67-56-1 methanol 
• 2584-71-6 cis-hydroxy-D-proline 
• 75-36-5 acetyl chloride 
• 1064036-63-0 (2R,4R)-4-Hydroxy-pyrrolidine-2-carbonyl chloride 
• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 444313-67-1 (1R,4R)-5-acetyl-2-oxa-5-azabicyclo[2.2.1]heptan-3-one 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 850741-35-4 methyl (2R,4R)-4-hydroxy-1-{2-[tris(4-methoxyphenyl)methoxy]-1-ethyl}pyrrolidine-2-carboxylate 
• 796095-60-8 (2S)-1-tert-butoxycarbonyl-2-(methoxycarbonyl)-4-hydroxyazacyclopentane 
• 1096711-36-2 methyl (2R,4R)-4-hydroxy-1-[[methyl(phenoxycarbonyl)amino]acetyl]pyrrolidine-2-carboxylate 
• 787640-34-0 (2R,4R)-1-benzyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate 
• 787640-35-1 (2R,4R)-benzyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 787640-36-2 (2R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate 
• 787640-37-3 (1R,4R)-benzyl 2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 661470-56-0 (1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1318129-73-5 methyl (2R,4R)-4-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2-carboxylate 
• 1318128-92-5 tert-butyl [(3S,5S)-5-azido-1-tritylpiperidin-3-yl]carbamate 
• 1318128-94-7 C₂₉H₃₃N₅O₂ 
• 1318128-88-9 tert-butyl [(3S,5R)-5-(azidomethyl)-1-(4-methoxybenzyl)pyrrolidin-3-yl]carbamate 
• 1318128-86-7 tert-butyl [(3S,5S)-5-azido-1-(4-methoxybenzyl)piperidin-3-yl]carbamate 
• 1318128-70-9 tert-butyl (3S,5R)-5-(hydroxymethyl)-1-tritylpyrrolidin-3-ylcarbamate 

Relevant articles and documents

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Concise synthesis of (2R,4R)-monatin

Monatin, 4-hydroxy-4-(3-indolylmethyl)-glutamic acid, is a naturally occurring sweet amino acid. The (2R,4R)-monatin isomer has been found to be the sweetest among its four stereoisomers. A concise and efficient synthesis of (2R,4R)-monatin was accomplished by the alkylation of (4R)-N-tert-butoxycarbonyl (tBoc)-4-tert-butyldimethylsilyoxy-D-pyroglutamic acid methyl ester with tert-butyl 3-(bromomethyl)-1H-indole-1-carboxylate to give (4R)-N-tBoc-4-tert-butyldimethylsilyloxy-4-(N-tBoc-3-indolylmethyl)-D-pyroglutamic acid methyl ester, i.e., the lactam form of (2R,4R)-monatin with protecting groups. This was followed by the hydrolysis of the lactam ring and deprotection. The 4-hydroxyl D-pyroglutamic acid derivative was demonstrated to be a suitable precursor for the efficient preparation of (2R,4R)-monatin in high optical purity because the alkylation proceeded in regioselective and stereoselective manners at C4 to form appropriate asymmetric tetra-substituted carbon center; the resulting alkylated pyroglutamic acid derivative was then easily converted into the linear form of monatin.