1622-20-4

Usage

Uses

Used in Pharmaceutical Industry:
(2R,4S)-4-hydroxypiperidine-2-carboxylic acid is used as a key intermediate in the synthesis of heterocyclic carboxamides, which are known as Ceramide Galactosyltransferase inhibitors. These inhibitors play a crucial role in modulating cellular processes and have potential applications in the treatment of various diseases, including cancer and neurodegenerative disorders.
In the preparation of Ceramide Galactosyltransferase inhibitors, (2R,4S)-4-hydroxypiperidine-2-carboxylic acid is used as a starting material or a building block to construct the desired heterocyclic carboxamides. The compound's hydroxy and carboxylic acid functional groups allow for further chemical modifications and the formation of the target molecules with desired biological activities.
The development of Ceramide Galactosyltransferase inhibitors using (2R,4S)-4-hydroxypiperidine-2-carboxylic acid as a key component can lead to the discovery of novel therapeutic agents with improved efficacy and selectivity. These inhibitors can potentially be used in the treatment of various diseases by modulating the levels of ceramide, a bioactive sphingolipid involved in cell signaling and apoptosis.

InChI:InChI=1/C6H11NO3/c8-4-1-2-7-5(3-4)6(9)10/h4-5,7-8H,1-3H2,(H,9,10)/t4-,5-/m1/s1

Upstream product

• 126774-16-1 cis-4-hydroxy-1,2-piperidinedicarboxylic acid 1-ethyl, 2-methyl ester 
• 106275-36-9 trans-4-hydroxy-N-tosyl-piperidine-2-carboxylic acid 
• 135690-64-1 (But-3-enyl-ethoxycarbonyl-amino)-hydroxy-acetic acid methyl ester 
• 135690-69-6 trans-4-formyloxy-1,2-piperidinedicarboxylic acid 1-ethyl, 2-methyl ester 
• 126774-13-8 acetoxyacetic acid methyl ester 
• 126778-08-3 2-acetamido-6-O-acetyl-2,3,5-trideoxy-D,L-threo-hexono-1,4-lactone 

Relevant academic research and scientific papers

2-Keto-3-Deoxy-l-Rhamnonate Aldolase (YfaU) as Catalyst in Aldol Additions of Pyruvate to Amino Aldehyde Derivatives

4-Hydroxy-2-keto acid derivatives are versatile building blocks for the synthesis of amino acids, hydroxy carboxylic acids and chiral aldehydes. Pyruvate aldolases are privileged catalysts for a straightforward access to this class of keto acid compounds. In this work, a Class II pyruvate aldolase from Escherichia coli K-12, 2-keto-3-deoxy-l-rhamnonate aldolase (YfaU), was evaluated for the synthesis of amino acid derivatives of proline, pipecolic acid, and pyrrolizidine-3-carboxylic acid. The aldol addition of pyruvate to N-protected amino aldehydes was the key enzymatic aldol addition step followed by catalytic intramolecular reductive amination. The corresponding N-Cbz-amino-4-hydroxy-2-keto acid (Cbz=benzyloxycarbonyl) precursors were obtained in 51–95% isolated yields and enantioselectivity ratios from 26:74 to 95:5, with chiral α-substituted N-Cbz-amino aldehydes. (S)-N-Cbz-amino aldehydes gave aldol adducts with preferentially (R)-configuration at the newly formed stereocenter, whereas the contrary is true for (R)-N-Cbz-amino aldehydes. Addition reactions to achiral amino aldehydes rendered racemic aldol adducts. Molecular models of the pre-reaction ternary complexes YfaU-pyruvate enolate-acceptor aldehyde were constructed to explain the observed stereochemical outcome of the reactions. Catalytic reductive amination of the aldol adducts yielded 4-hydroxy-2-pipecolic acid, and unprecedented C-5 substituted 4-hydroxyproline and pyrrolizidine-3-carboxylic acid derivatives. (Figure presented.).

A concise and diastereoselective synthesis of piperidine and indolizidine alkaloids via aza-Prins cyclization

The synthesis of 2-substituted and 2,4-disubstituted piperidine alkaloids such as (±)-coniine, (±)-hydroxypipecolic acid, (±)-pipecolic acid, (±)-coniceine, and (±)-4-hydroxy-2- hydroxy-methyl piperidine have been accomplished in a highly diastereo-selective manner by employing aza-Prins cyclization as a key step to construct the piperidine core of these alkaloids. Georg Thieme Verlag Stuttgart · New York.

Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine

An expeditious synthesis of cis-4-hydroxypipecolic acid (1) is described. The key step was diastereoselective hydrogenation of 2-acetamido-6-O-acetyl-2,3,5-trideoxy-hex-2-enono-1,4-lactone (3), obtained in three high yielding steps from D-glucosamine. The

FORMIC ACID-INDUCED ?-CYCLIZATION OF GLYCINE CATION EQUIVALENTS TO SUBSTITUTED PIPECOLIC ACID DERIVATIVES

Formic acid-mediated cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)-acetoxyglycine esters are described.The major reaction products are 4-formyloxypipecolic acid derivatives, formed with low stereoselectivity at C-4.The several subtle features of the cyclization process are satisfactorily explained by a mechanism involving (1) a rapid cationic aza-Cope rearrangement of the incipient iminium ion and (2) participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

TIN TETRACHLORIDE-INDUCED ?-CYCLIZATIONS OF GLYCINE CATION EQUIVALENTS TO SUBSTITUTED PIPECOLIC ACID DERIVATIVES

Cationic ?-cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)acetoxyglycine esters induced by tin tetrachloride in dichloromethane are described.Reactions started and quenched with water at -78 deg C mainly yield cis-4-hydroxypipecolic esters, whereas reactions quenched after warm-up to room temperature provide trans-4-chloropipecolic esters as major products.A mechanistic scheme is advanced which adequately explains these results.The essentials are a rapid cationic aza-Cope equilibrium of the incipient iminium cation, and participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.