(2S,5R)-5-hydroxypiperidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,5R)-5-hydroxypiperidine-2-carboxylic acid
• CAS No.: 50439-45-7
• Molecular Formula: C6H11NO3
• Molecular Weight: 145.158
• Hs Code.: 2933399090
• UNII: N38XA45QRV
• DSSTox Substance ID: DTXSID001302217
• Nikkaji Number: J664.550J
• Wikidata: Q105238374
• Mol file: 50439-45-7.mol

Synonyms:50439-45-7;(2S,5R)-5-Hydroxypipecolic acid;(2S,5R)-5-hydroxypiperidine-2-carboxylic acid;(2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid;trans-5-Hydroxy-L-pipecolic acid;N38XA45QRV;2-Piperidinecarboxylic acid, 5-hydroxy-, (2S,5R)-;L-trans-5-Hydroxypipecolic acid;5-Hydroxy-L-pipecolic acid, trans-;5-Hydroxy-L-pipecolic acid, trans-(-)-;UNII-N38XA45QRV;2-Pyrimidinecarboximidamide HCl;SCHEMBL1250475;DTXSID001302217;AKOS006351657;AMY202003234;CS-0138319;A902404;W-201171

Chemical Property of (2S,5R)-5-hydroxypiperidine-2-carboxylic acid

Chemical Property:

• Boiling Point: 354.8±42.0 °C(Predicted)
• PKA: 2.31±0.40(Predicted)
• PSA: 69.56000
• Density: 1.299
• LogP: -0.48730
• XLogP3: -3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 145.07389321
• Heavy Atom Count: 10
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

(2S,5R)-5-Hydroxypipecolicacid 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NCC1O)C(=O)O
• Isomeric SMILES: C1C[C@H](NC[C@@H]1O)C(=O)O

Technology Process of (2S,5R)-5-hydroxypiperidine-2-carboxylic acid

There total 12 articles about (2S,5R)-5-hydroxypiperidine-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: 61.0%

pipecolinic acid (3105-95-1,83680-83-5) → (2S,5R)-5-hydroxy-2-piperidinecarboxylic acid (50439-45-7,448964-01-0,478409-64-2)

Guidance literature:

With iron(II) sulfate; α-ketoglutaric acid disodium salt; In culture medium; at 28 ℃; for 72h; regioselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.201000863

Reference yield: 44.0%

δ-hydroxylysine hydrochloride (2219-28-5) → (2S,5R)-5-hydroxy-2-piperidinecarboxylic acid (50439-45-7,448964-01-0,478409-64-2) + (2S,5R)-5-hydroxypiperidine-2-carboxylic acid (63088-78-8,448964-01-0,478409-64-2)

Guidance literature:

With D-glucose; nicotinamide adenine dinucleotide phosphate; sodium hydroxide; In water; at 30 ℃; pH=8; Enzymatic reaction;

Reference yield:

2,6-diamino-5-hydroxy-hexanoic acid (504-91-6,1190-94-9,3506-26-1,6000-08-4,18899-29-1,18899-30-4,18899-31-5,52153-41-0,78088-29-6,28902-93-4) → (2S,5R)-5-hydroxy-2-piperidinecarboxylic acid (50439-45-7,448964-01-0,478409-64-2) + (2S,5R)-5-hydroxypiperidine-2-carboxylic acid (63088-78-8,448964-01-0,478409-64-2)

Guidance literature:

Enzymatic reaction;

upstream raw materials:

rac-(2R*,5S*)-5-hydroxypiperidine-2-carboxylic acid

(2S,5R)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid

pipecolinic acid

benzyloxycarbonyl-L-baikiain

Downstream raw materials:

(2S,5R)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid

(2S,5R)-5-hydroxy-2-piperidinecarboxylic acid

2R,5S-5-hydroxy-piperidine-2-carboxylic acid

(2S,5R)-methyl 5-hydroxypiperidine-2-carboxylate

Refernces

• 1、 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.
• 2、 Klein, Christian,Huettel, Wolfgang. "A simple procedure for selective hydroxylation of L -proline and l -pipecolic acid with recombinantly expressed proline hydroxylases". experimental part. p. 1375 - 1383. Retrieved 2011/06/26.