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

Base Information

• Chemical Name: (2S,3R)-3-hydroxypyrrolidine-2-carboxylic acid
• CAS No.: 567-35-1
• Deprecated CAS: 1855-80-7,19246-26-5,29887-44-3
• Molecular Formula: C₅H₉NO₃
• Molecular Weight: 131.131
• UNII: 11L19HLQ3S
• DSSTox Substance ID: DTXSID70427760
• Nikkaji Number: J191.773K
• Wikidata: Q27124321
• Metabolomics Workbench ID: 58860
• Mol file: 567-35-1.mol

Synonyms:567-35-1;(2S,3R)-3-hydroxypyrrolidine-2-carboxylic acid;cis-3-hydroxy-L-proline;Cis-l-3-hydroxyproline;cis-3-Hydroxyproline;cis-3-Hydroxy-dl-proline;(3R)-3-hydroxy-L-proline;4298-05-9;(2S,3R)-3-HYDROXYPROLINE;L-Proline, 3-hydroxy-, (3R)-;11L19HLQ3S;Proline, 3-hydroxy-, L-cis-;3-Hydroxy-L-proline, (3R)-;(2S,3R)-(-)-3-Hydroxy-L-proline;Cis-3-hydroxypyrrolidine-2-carboxylic acid;(2~{S},3~{R})-3-oxidanylpyrrolidine-2-carboxylic acid;DL-cis-Hydroxyproline;SCHEMBL7412;UNII-11L19HLQ3S;(2S,3R)-3-Hydroxy-pyrrolidine-2-carboxylic acid;CHEBI:55479;DTXSID70427760;BJBUEDPLEOHJGE-DMTCNVIQSA-N;cis-3-Hydroxy-DL-proline, 95%;AMY15345;CS-M2136;cis-L-3-Hydroxyproline, AldrichCPR;MFCD06796744;AKOS006280740;DS-4888;Cis-3-hydroxypyrrolidine-2-carboxylicacid;C19706;EN300-741867;(+/-)-cis-3-Hydroxypyrrolidine-2-carboxylic acid;A856283;rac-(2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid;Q27124321;1-[6-(tert-Butyl)-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]ethan-1-oneoxime;G8X

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

Chemical Property:

• Melting Point: 221-228℃ (dec.) (ethanol water )
• Boiling Point: 355.2±42.0 °C(Predicted)
• PKA: 2.03±0.40(Predicted)
• PSA: 69.56000
• Density: 1.395±0.06 g/cm3 (20 ºC 760 Torr)
• 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:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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: cis-L-3-Hydroxyproline is a versatile building block, used in the synthesis of various pharmaceutical and biologically active compounds. It is an isomer to trans-3-Hydroxyproline (H950925).

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

There total 31 articles about (2S,3R)-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:

(2S,3S,4R)-3,4-dihydroxy-L-proline

3,4-dihydroxy-l-proline

cis-3-hydroxy-L-proline methyl ester

(2S,3R)-N-tert-Butyloxycarbonyl-3-hydroxy-2-pyrrolidinecarboxylic Acid Methyl Ester