(2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid
• CAS No.: 4298-08-2
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• Hs Code.: 29339980
• Nikkaji Number: J722.339K
• Wikidata: Q27159975
• Metabolomics Workbench ID: 38027
• Mol file: 4298-08-2.mol

Synonyms:(2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid;118492-86-7;cis-3-hydroxy-d-proline;3-Hydroxyproline;cis-3-Hydroxy-dl-proline;3-HYDROXY-L-PROLINE;(+)-cis-(2R,3S)-3-hydroxyproline;4298-05-9;D-Proline, 3-hydroxy-, (3S)-;Cis-3-hydroxypyrrolidine-2-carboxylic acid;3beta-Hydroxy-D-proline;(3S)-3-hydroxy-D-proline;(2R,3S)-3-Hydroxy-pyrrolidine-2-carboxylic acid;SCHEMBL2025245;cis-(2R,3S)-3-hydroxyproline;CHEBI:88157;BJBUEDPLEOHJGE-IUYQGCFVSA-N;MFCD00143991;MFCD09996919;Procollagen trans-3-hydroxy-L-proline;AS-50693;cis-3-Hydroxy-pyrrolidine-2-carboxylic acid;CS-0053473;(2R,3S)-3-hydroxypyrrolidine-2-carboxylicacid;P10890;(+)-cis-3-hydroxypyrrolidine-2-carboxylic acid;cis-3-Hydroxy-DL-proline (H-DL-Pro(3-OH)-OH);Q27159975

Chemical Property of (2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid

Chemical Property:

• Appearance/Colour: White to light beige powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 235oC
• Refractive Index: 1.54
• Boiling Point: 355.233 °C at 760 mmHg
• PKA: 2.03±0.40(Predicted)
• Flash Point: 168.639 °C
• PSA: 69.56000
• Density: 1.395g/cm³
• LogP: -0.87740
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 131.058243149
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-3-Hydroxy-L-proline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C1O)C(=O)O
• Isomeric SMILES: C1CN[C@H]([C@H]1O)C(=O)O
• Uses: trans-3-Hydroxyproline, is a versatile building block, used in the synthesis of various pharmaceutical and biologically active compounds. It is used as an intermediate in the synthesis of ferrocene-hydroxyproline amino acid conjugates.

Technology Process of (2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid

There total 61 articles about (2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (2S,3R)-3-hydroxyproline (567-35-1,567-36-2,4298-05-9,4298-06-0,4298-08-2,14916-76-8,62182-84-7,104069-26-3,118492-86-7,119677-21-3)

Guidance literature:

With ferrous(II) sulfate heptahydrate; cis-3-proline hydroxylase type II; sodium L-ascorbate; at 37 ℃; for 16h; stereospecific reaction;

DOI:10.3762/bjoc.7.193

Reference yield: 98.0%

(2S,3R)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (1262015-07-5) → (2S,3R)-3-hydroxyproline (567-35-1,567-36-2,4298-05-9,4298-06-0,4298-08-2,14916-76-8,62182-84-7,104069-26-3,118492-86-7,119677-21-3)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; at 25 ℃; for 12h; under 4137.29 Torr;

DOI:10.1016/j.tetlet.2010.10.086

Reference yield: 90.0%

(2S,3R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)pyrrolidine-2-carboxylic acid (166383-67-1) → (2S,3R)-3-hydroxyproline (567-35-1,567-36-2,4298-05-9,4298-06-0,4298-08-2,14916-76-8,62182-84-7,104069-26-3,118492-86-7,119677-21-3)

Guidance literature:

(2S,3R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)pyrrolidine-2-carboxylic acid; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

With methyloxirane; In methanol; at 20 ℃; for 2h;

upstream raw materials:

cis-(3R)-(tert-butyldimethylsilyloxy)-2-cyano-1-methoxycarbonyl-3-pyrrolidine

(2S,3R)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

(2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carboxylic acid

Downstream raw materials:

N-[(3-cyanobenzene)sulfonyl]-(3S)-hydroxy-(L)-proline methyl ester

(2S,3S)-1-((benzyloxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

(2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

2-benzyl 1-(tert-butyl) (2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate

Refernces

• 1、 Durand, Jean-Olivier,Larcheveque, Marc,Petit, Yves. "Reductive cyanation: A key step for a short synthesis of (-)-(2S,3S)-3- hydroxyproline". . p. 5743 - 5746. Retrieved 1998.
• 2、 Zwick, Christian R.,Sosa, Max B.,Renata, Hans. "Modular Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues Enables Elucidation of Its Key Pharmacophores". supporting information. p. 1673 - 1679. Retrieved 2021/01/25.
• 3、 Smart, Tristan J.,Hamed, Refaat B.,Claridge, Timothy D.W.,Schofield, Christopher J.. "Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles". supporting information. . Retrieved 2019/11/26.