3-Hydroxyproline

Base Information

• Chemical Name: 3-Hydroxyproline
• CAS No.: 14916-76-8
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• DSSTox Substance ID: DTXSID20276427
• Nikkaji Number: J413.965H
• Wikidata: Q27109279
• Mol file: 14916-76-8.mol

Synonyms:3-hydroxyproline;3-hydroxyproline, (L)-isomer;3-hydroxyproline, DL-(cis)-isomer;3-hydroxyproline, DL-(trans)-isomer;3-hydroxyproline, L-(cis)-isomer;3-hydroxyproline, L-(trans)-isomer

Chemical Property of 3-Hydroxyproline

Chemical Property:

• 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:

95% ^*data from raw 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](C1O)C(=O)O

Technology Process of 3-Hydroxyproline

There total 31 articles about 3-Hydroxyproline 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,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

Δ¹-pyrroline-5-carboxylic acid

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

(2S,3R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-3-(prop-2-yn-1-yloxy)pyrrolidine-2-carboxylic acid

Refernces

Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines

10.1021/ol702518t

The research focuses on the construction of epidithiodioxopiperazines (ETPs), which are toxic secondary metabolites produced by fungi, through a novel synthetic method. The purpose of the study was to develop a regioselective C-H bond oxidation process directed by a proximal (bromomethyl)silyl group, which is a key step in the synthesis of ETPs. The researchers successfully developed a method for constructing tricyclic epidithiodioxopiperazines from dioxopiperazines containing a hydroxyproline unit. The process involved the use of various chemicals, including 3-hydroxyproline derivatives, acetylglycolic acid, dioxopiperazine diacetate, and a (bromomethyl)dimethylsilyl-protecting/radical-translocating group. The conclusions of the research were that a selective oxidation of the angular methine carbon of hydroxyproline-derived dioxopiperazines was achieved, allowing the introduction of a dithio bridge into such heterocyclic frameworks. This protecting-group-directed C-H bond oxidation is likely to be useful for the regioselective oxidative elaboration of other polyfunctional organic molecules.

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