154307-84-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,5S)-5-hydroxypiperidine-2-carboxylic acid hydrochloride is utilized as a key building block in the development of new drugs and therapeutic agents. Its unique structure and improved water solubility contribute to the creation of effective pharmaceutical compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2S,5S)-5-hydroxypiperidine-2-carboxylic acid hydrochloride serves as an important intermediate for the synthesis of various organic compounds. Its properties allow for the development of innovative molecules with potential applications in medicine and healthcare.

Upstream product

• 138565-95-4 methyl (2S,5S)-5-hydroxy-N-methoxycarbonyl-piperidine-2-carboxylate 
• 24211-54-9 (S)-5-hydroxypiperidin-2-one 
• 87179-81-5 (-)-(5S)-5-(tert-butyldimethylsilanyloxy)piperidin-2-one 
• 138565-91-0 (5S)-methyl 5-(tert-butyldimethylsilanyloxy)-2-oxopiperidine-1-carboxylate 
• 154049-26-0 (5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-2-methylene-piperidine 
• 154049-27-1 (2S,5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-2-hydroxymethyl-piperidine 
• 154049-28-2 (2S,5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-2-hydroxymethyl-piperidine 
• 154049-29-3 methyl (2S,5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-piperidine-2-carboxylate 
• 32159-21-0 Cbz-L-pGlu-OH 
• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 147489-30-3 (2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 169825-97-2 N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester 
• 1383814-52-5 (2S,5S)-tert-butyl 5-hydroxypiperidine-2-carboxylate 
• 1253856-42-6 (2S,5S)-di-tert-butyl 5-hydroxypiperidine-1,2-dicarboxylate 

Downstream Products

• 1487347-86-3 (2S,5S)-N-tert-butoxycarbonyl-5-hydroxy-2-carboxylic acid piperidine 
• 1426573-07-0 (2S,5R)-1-[(1,1-dimethylethyl)carbonyl]-5-[(benzyloxy)amino]piperidine-2-carboxylic acid 
• 1452458-86-4 RG₆₀₈₀ 
• 1452466-19-1 {2-[({[(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamic acid tert-butyl ester 
• 1452466-57-7 (2S,5R)-6-(benzyloxy)-N-methoxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1452467-32-1 (2S,5R)-6-(benzyloxy)-7-oxo-N’-propanoyl-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 
• 1426572-71-5 (2S,5R)-N’-acetyl-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 
• 1383814-58-1 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid methyl ester 
• 1416134-73-0 (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester 
• 1174020-25-7 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 

Relevant academic research and scientific papers

A New Synthesis of l -Hydroxypipecolic Acid

A new synthetic approach toward l -hydroxypipecolic acid is described. This reaction sequence involves eight steps overall, starting from commercially available and inexpensive l -glyceraldehyde acetal. The strategy makes use of readily available reagents and can be used as a preparative synthesis of l -hydroxypipecolic acid. Most of the reaction steps proceed with moderate-to-good yields and do not require any unusual or expensive reagents.

Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar αvβ3 integrin ligand

A stereodivergent strategy was devised to obtain enantiopure cis and trans 5-aminopipecolic acids (5-APAs) in suitably protected forms to be employed in peptide synthesis as conformationally constrained α- and δ-amino acids. The cis isomer was used as a δ-amino acid to construct a cyclic RGD-containing peptidomimetic, the ability of which to compete with biotinylated vitronectin for binding with the isolated αVβ3 integrin was measured (IC50 = 4.2 ± 0.9 nM). A complete 1H NMR and computational conformational analysis was performed to elucidate the reasons for the high affinity of this cyclic peptidomimetic in comparison with cilengitide.

METHOD FOR PRODUCING 5-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID

A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).

Macrocyclic inhibitors of the PD-1/PD-L1 and CD80(B7-1)/PD-L1 protein/protein interactions

The present disclosure provides novel macrocyclic peptides which inhibit the PD-1/PD-L1 and PD-L1/CD80 protein/protein interaction, and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

NOVEL -LACTAMASE INHIBITOR AND METHOD FOR PRODUCING SAME

The currently available β-lactamase inhibitors are insufficient to inhibit the incessantly increasing β-lactamase, and novel β-lactamase inhibitors has been required today for the difficult treatment for bacterial infectious diseases caused by resistant bacteria which produce class C β-lactamase, extended-spectrum β-lactamase (ESBL) belonging to class A and D, or class A KPC-2 decomposing even carbapenem as a last resort for β-lactam antibiotic. A compound represented by the the formula (I), preparation process of the same, β-lactamase inhibitors and method for treating bacterial infectious diseases are provided.

Synthesis of 2S,5S- and 2R,5S-5-hydroxypipecolic acid via amide-methylenation of S-5-hydroxy-2-piperidone with dimethyltitanocene

A route to 2S,5S-hydroxypipecolic acid is presented, starting with the enantiopure 5S-5-hydroxy-piperidone 7. The key step of this reaction sequence is the chemoselective methylation of the amide carbonyl group of 8 with dimethyltitanocene 9 to 10. The tr