trans-4-Hydroxy-D-proline

Base Information

• Chemical Name: trans-4-Hydroxy-D-proline
• CAS No.: 3398-22-9
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• Hs Code.: 29339900
• NSC Number: 524341,122285,206304,206274,206273
• DSSTox Substance ID: DTXSID60861573
• Nikkaji Number: J4.116E
• Wikidata: Q411237
• ChEMBL ID: CHEMBL1213475
• Mol file: 3398-22-9.mol

Synonyms:D-Proline,4-hydroxy-, trans-;(2R,4S)-(+)-4-Hydroxy-D-proline;4-(S)-Hydroxypyrrolidine-2-(R)-carboxylic acid;D-Hydroxyproline;D-trans-4-Hydroxyproline;NSC 206273;trans-4-Hydroxy-D-proline;

Chemical Property of trans-4-Hydroxy-D-proline

Chemical Property:

• Appearance/Colour: White crystal or crystalline powder
• Vapor Pressure: 1.8E-06mmHg at 25°C
• Melting Point: 260°C
• Refractive Index: 1.54
• Boiling Point: 355.2 °C at 760 mmHg
• PKA: 2.14±0.40(Predicted)
• Flash Point: 168.6 °C
• PSA: 69.56000
• Density: 1.395 g/cm³
• LogP: -0.87740
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -3.3
• 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:

99.0% ^*data from raw suppliers

trans-D-4-Hydroxyproline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 24/25-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1C(CNC1C(=O)O)O

Technology Process of trans-4-Hydroxy-D-proline

There total 13 articles about trans-4-Hydroxy-D-proline 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: 79.0%

(2R,4S)-4-(benzyloxy)-1-N-tosylpyrrolidine-2-carboxylic acid → trans-4-hydroxyproline (3398-22-9,30724-02-8)

Guidance literature:

With ammonia; sodium; at -70 ℃; for 3.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152081

Reference yield:

→ trans-4-hydroxyproline (3398-22-9,30724-02-8)

Guidance literature:

With ammonia; at 95 - 100 ℃;

Reference yield:

N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline (77449-96-8) → trans-4-hydroxyproline (3398-22-9,30724-02-8)

Guidance literature:

With sodium hydroxide; Erhitzen des Reaktionsprodukts mit wss. HCl;

upstream raw materials:

N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline

trans-1-(3,5-dinitro-benzoyl)-4-hydroxy-D-proline

trans-4-hydroxy-D,L-proline

N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline Methyl Ester

Downstream raw materials:

6-hydroxy-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

4-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid

4-Hydroxy-1-propyl-pyrrolidine-2-carboxylic acid

(4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline

Refernces

• 1、 Lacasta, Susana,Sebastian, Victor,Casado, Clara,Mayoral, Alvaro,Romero, Pilar,Larrea, Angel,Vispe, Eugenio,Lopez-Ram-De-Viu, Pilar,Uriel, Santiago,Coronas, Joaquin. "Chiral imprinting with amino acids of ordered mesoporous silica exhibiting enantioselectivity after calcination". scheme or table. p. 1280 - 1287. Retrieved 2012/02/15.