(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:

97% ^*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
• General Description: (2S,5R)-trans-5-Hydroxypipecolic acid is a naturally occurring non-proteinogenic amino acid characterized by a piperidine ring with hydroxyl and carboxylic acid functional groups at the 5- and 2-positions, respectively, in a trans configuration. It serves as a key structural motif in various alkaloids and bioactive compounds found in plants and microorganisms. (2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid can be synthesized diastereoselectively through methods involving epoxidation of cyclic enamide intermediates and N-acyliminium ion chemistry, enabling the introduction of substituents at the 6-position. Its derivatives are of interest due to their biological relevance and potential applications in medicinal chemistry.

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

Diastereoselective synthesis of (2Ss,5R)-5-hydroxypipecolic acid and 6-substituted derivatives

10.1021/ol047774v

The study presents a diastereoselective synthesis method for the natural product (2S,5R)-5-hydroxypipecolic acid and its 6-substituted derivatives. The key step involves a highly diastereoselective epoxidation reaction of an enantiomerically pure cyclic enamide intermediate. Chemicals used include L-allysine ethylene acetal 4, Cbz-OSu for N-carbonylation, MeI for methylation, ptoluenesulfonic acid for cyclization-elimination, and oxone for epoxidation. The synthesis also involves N-acyliminium ion chemistry for the introduction of substituents at the 6-position. These chemicals serve to protect the amino acid, facilitate cyclization, and achieve the desired diastereoselectivity in the formation of the target compounds, which are important due to their presence in various plants, microorganisms, and as the core structure of numerous naturally occurring alkaloids.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 50439-45-7 (2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid

Send

Send

Metric Ton KG G Pound L ML

Send

Send