cis-4-Hydroxy-D-proline

Base Information

• Chemical Name: cis-4-Hydroxy-D-proline
• CAS No.: 2584-71-6
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• Hs Code.: 29339900
• Mol file: 2584-71-6.mol

Synonyms:D-Proline,4-hydroxy-, cis-;Proline, 4-allo-hydroxy-, D- (8CI);(2R,4R)-4-Hydroxypyrrolidine-2-carboxylic acid;(4R)-4-Hydroxy-D-proline;4-(R)-Hydroxypyrrolidine-2-(R)-carboxylic acid;4-Hydroxy-D-alloproline;4-allo-Hydroxy-D-proline;D-allo-4-Hydroxyproline;NSC 524341;D-cis-Hydroxyproline;

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

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.8E-06mmHg at 25°C
• Melting Point: 243 °C (dec.)(lit.)
• 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.: Store at RT.
• Solubility.: Water (Slightly)
• Water Solubility.: 5 g/100 mL
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 131.058243149
• Heavy Atom Count: 9
• Complexity: 120

Purity/Quality:

99% ^*data from raw suppliers

cis-4-Hydroxy-D-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-22-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C[NH2+]C1C(=O)[O-])O
• Isomeric SMILES: C1[C@H](C[NH2+][C@H]1C(=O)[O-])O
• Uses: cis-4-Hydroxy-D-proline (cas# 2584-71-6) is a compound useful in organic synthesis.

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

There total 29 articles about cis-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: 96.0%

4R-4-hydroxyproline (51-35-4,30724-02-8) → cis-hydroxy-D-proline (2584-71-6,30724-02-8)

Guidance literature:

4R-4-hydroxyproline; With acetic anhydride; In acetic acid; for 5.5h; Heating;

With hydrogenchloride; for 3h; Heating;

DOI:10.1016/j.tetasy.2003.08.019

Reference yield: 75.0%

(1R,4R)-5-acetyl-2-oxa-5-azabicyclo[2.2.1]heptan-3-one (444313-67-1,87304-67-4) → cis-hydroxy-D-proline (2584-71-6,30724-02-8)

Guidance literature:

With hydrogenchloride; for 2h; Heating;

DOI:10.1016/S0957-4166(02)00074-5

Reference yield: 75.0%

(2R,4R)-4-<(tert-Butyl)dimethylsilyloxy>-2-cyanopyrrolidin-1-carbonsaeure-methylester (108782-06-5) → cis-hydroxy-D-proline (2584-71-6,30724-02-8)

Guidance literature:

With hydrogenchloride; for 17h; Heating;

DOI:10.1002/hlca.19860690726

upstream raw materials:

acetic anhydride

acetic acid

4R-4-hydroxyproline

(2R,4R)-4-<(tert-Butyl)dimethylsilyloxy>-2-cyanopyrrolidin-1-carbonsaeure-methylester

Downstream raw materials:

(R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline

1N-[4-(4-Fluorophenoxy)phenyl]sulfonyl-4R-hydroxy-pyrrolidine-2R-carboxylic acid

(2R,4R)-4-Hydroxy-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylic acid

Refernces

• 1、 Fujita. "-". . p. 1379. Retrieved 1960.
• 2、 Ganesh, Krishna N,More, Shahaji H. "Spiegelmeric 4R/S-hydroxy/amino-L/D-prolyl collagen peptides: conformation and morphology of self-assembled structures". . . Retrieved 2020/03/11.
• 3、 Cheong, Jae Eun,Pfeiffer, Conrad T.,Northrup, Justin D.,Parker, Matthew F.L.,Schafmeister, Christian E.. "An improved, scalable synthesis of bis-amino acids". supporting information. p. 4882 - 4884. Retrieved 2016/10/24.