178962-09-9

Basic information

• Product Name: D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)
• Synonyms: D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI);D-Proline,4-hydroxy-,methyl ester,(4S)-;4S)-Methyl 4-hydroxypyrrolidine-2-carboxylate;(S)-4-Hydroxy-D-proline Methyl Ester;(2R,4S)-Methyl 4-hydroxypyrrolidine-2-carboxylate HCl
• CAS NO: 178962-09-9
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.15644
• Product Categories: CARBOXYLICESTER
• Mol File: 178962-09-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 247.2±40.0 °C(Predicted)
• Appearance: /
• Density: 1.216±0.06 g/cm3(Predicted)
• PKA: 14.44±0.40(Predicted)
• CAS DataBase Reference: D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)(178962-09-9)
• EPA Substance Registry System: D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)(178962-09-9)

Safety Data

• Hazardous Substances Data: 178962-09-9(Hazardous Substances Data)

Usage

General Description

D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) is a chemical compound that belongs to the class of proline derivatives. It is a methyl ester of 4-hydroxy-D-proline, which is a naturally occurring amino acid found in collagen and other proteins. D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) has potential applications in the pharmaceutical industry, particularly in the synthesis of peptidomimetic compounds and as a building block for the development of novel drugs. Its stereochemistry, with a 4S configuration, is important for its specific biological and chemical properties, making it a valuable molecule for various research and industrial applications.

Upstream product

• 67-56-1 methanol 
• 3398-22-9 trans-4-hydroxyproline 

Downstream Products

• 102195-80-2 (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 506406-70-8 (3S,5R)-1-benzyl-3-(tert-butyldimethylsilyloxy)-5-hydroxymethylpyrrolidine 
• 1932056-72-8 tert-butyl (3R,5R)-3-amino-5-fluoropiperidine-1-carboxylate 
• 1216941-64-8 (2S,6S,13aS,14aR,16aS,Z)-ethyl 2-(4-bromophenylsulfonyloxy)-6-(tert-butoxycarbonylamino)-5,16-dioxo-1,2,3,5, 6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydronaphthylcyclopropanoyl[e]pyrrolo[1,2-a][1,4] diazacyclopentadecyne-14a-carboxylate 
• 1611481-26-5 (R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone 
• 1611481-21-0 tert-butyl (3R,5S)-5-hydroxypiperidin-3-ylcarbamate 
• 1611481-20-9 tert-butyl ((3S,5R)-1-benzyl-5-hydroxypiperidin-3-yl)carbamate 
• 1611481-18-5 tert-butyl (3R,5R)-1-benzyl-5-(hydroxymethyl)pyrrolidin-3-ylcarbamate 
• 1611481-16-3 (2R,4R)-methyl 4-azido-1-benzylpyrrolidine-2-carboxylate 
• 627101-16-0 (2R,4R)-(4-amino-1-benzylpyrrolidin-2-yl)methanol 
• 114676-54-9 (2R,4R)-1-benzyl-2-carbomethoxy-4-<(methylsulfonyl)oxy>pyrrolidine 
• 1611488-11-9 (R)-N-(5,5-difluoropiperidin-3-yl)benzamide 
• 647857-51-0 (2R,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate 

Relevant articles and documents

Enantioselective synthesis and physicochemical properties of libraries of 3-amino- and 3-amidofluoropiperidines

The enantioselective syntheses of 3-amino-5-fluoropiperidines and 3-amino-5,5-difluoropiperidines were developed using the ring enlargement of prolinols to access libraries of 3-amino- and 3-amidofluoropiperidines. The study of the physicochemical properties revealed that fluorine atom(s) decrease(s) the pKa and modulate(s) the lipophilicity of 3-aminopiperidines. The relative stereochemistry of the fluorine atoms with the amino groups at C3 on the piperidine core has a small effect on the pK a due to conformationnal modifications induced by fluorine atom(s). In the protonated forms, the C-F bond is in an axial position due to a dipole-dipole interaction between the N-H+ and C-F bonds. Predictions of the physicochemical properties using common software appeared to be limited to determine correct values of pKa and/or differences of pK a between cis- and trans-3-amino-5-fluoropiperidines.

Part 3: Design and synthesis of proline-derived α2δ ligands

A potent series of substituted (2S,4S)-benzylproline α 2δ ligands have been designed from the readily available starting material (2S,4R)-hydroxy-l-proline. The ligands have improved pharmacokinetic profile over the (4S)-phenoxyproline derivati

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