(D-Proline, 3-hydroxy-, (3R)- )

Base Information

• Chemical Name: (D-Proline, 3-hydroxy-, (3R)- )
• CAS No.: 119677-21-3
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• Mol file: 119677-21-3.mol

Synonyms:trans-3-Hydroxy-D-proline;

Chemical Property of (D-Proline, 3-hydroxy-, (3R)- )

Chemical Property:

• Melting Point: 220-230 °C
• Boiling Point: 355.233 °C at 760 mmHg
• PKA: 2.03±0.40(Predicted)
• Flash Point: 168.639 °C
• PSA: 69.56000
• Density: 1.395 g/cm³
• LogP: -0.87740
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

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

(3R)-3-Hydroxy-D-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3R)-3-Hydroxy-D-proline is used in the synthesis of lysophosphatidylserine analogues as inducers of mast cell degranulation.

Technology Process of (D-Proline, 3-hydroxy-, (3R)- )

There total 43 articles about (D-Proline, 3-hydroxy-, (3R)- ) 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:

(3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-D-proline

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

3,4-dihydroxy-l-proline

cis-3-hydroxy-L-proline methyl ester

Refernces

• 1、 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.
• 2、 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.