4382-31-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,4S)-4-Hydroxypiperidine-2-carboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals, particularly those targeting the central nervous system. Its unique stereochemistry and functional groups enable the development of drugs with specific therapeutic effects.
Used in Drug Discovery and Development:
(2S,4S)-4-Hydroxypiperidine-2-carboxylic acid is utilized as a starting material in drug discovery and development processes. Its potential applications in the treatment of neurological disorders make it an attractive candidate for further research and optimization to improve its pharmacological properties.
Used in Organic Chemistry:
As a valuable building block in organic chemistry, (2S,4S)-4-Hydroxypiperidine-2-carboxylic acid is employed in the synthesis of various organic compounds and complex molecules. Its versatility and unique structural features contribute to the development of novel chemical entities with potential applications in various fields.

Upstream product

• 326477-58-1 (2S,4S)-(-)-4-Acetoxy-2-phenyl-1-trifluoroacetylpiperidine 
• 1103929-08-3 methyl (2S,4S)-4-hydroxypiperidine-2-carboxylate 
• 126774-16-1 cis-4-hydroxy-1,2-piperidinedicarboxylic acid 1-ethyl, 2-methyl ester 
• 126778-08-3 2-acetamido-6-O-acetyl-2,3,5-trideoxy-D,L-threo-hexono-1,4-lactone 
• 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 
• 653589-16-3 di(tert-butyl) (2S,4S)-4-hydroxy-6-oxo-1,2-piperidinedicarboxylate 
• 653589-35-6 di(tert-butyl) (2S,4R)-4-hydroxy-1,2-piperidinedicarboxylate 
• 653589-10-7 1,2-di-tert-butyl (2S)-4,6-dioxopiperidine-1,2-dicarboxylate 
• 475504-28-0 4-formyloxy-(S)-pipecolic acid methyl ester 
• 78553-47-6 methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate 

Downstream Products

• 100373-16-8 (2S)-1-benzoyl-4t-hydroxy-piperidine-2r-carboxylic acid 
• 1844-40-2 (2S,4R)-4-hydroxypiperidine-2-carboxylic acid 
• 441044-12-8 (2S,4S)-N-Boc-4-hydroxypiperidine-2-carboxylic acid 
• 917099-02-6 (2S,4S)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxy-2-piperidinecarboxylic acid 
• 98593-76-1 (+)-1-Acetyl-4-hydroxy-D-pipecolinsaeurelacton 
• 98593-76-1 4-Hydroxypipecolinsaeurelactonacetat 

Relevant academic research and scientific papers

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

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.

Validation of high-affinity binding sites for succinic acid through distinguishable binding of gamma-hydroxybutyric acid receptor-specific NCS 382 antipodes

Gamma-hydroxybutyric acid (GHB) binding to multiple sites for the tricarboxylic acid cycle intermediate succinic acid (SUC) has been disclosed recently. In order to better characterize these targets, distinguishable binding of GHB receptor-specific NCS 38

The synthesis of 4-hydroxypipecolic acids by stereoselective cycloaddition of configurationally stable nitrones

The diastereoselective synthesis of trans- and cis-4-hydroxypipecolic acids has been achieved with geometry-controlled nitrone cycloaddition chemistry. The cycloaddition of 3-butenol to enantiopure C-aminocarbonyl and C-alkoxycarbonyl nitrones having a de

Use of hydrolases for the synthesis of cyclic amino acids

The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. I

Chiral scaffolds and their preparation

A crystalline salt according to formula (1): or the opposite enantiomer thereof, wherein X+ is a cation. Such salts are useful in preparing chiral scaffolds, in particular of formulae (a)-(d).

Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-OtBu and other β-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy δ-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo- 1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).

Chemoenzymatic synthesis of the four diastereoisomers of 4-hydroxypipecolic acid from N-acetyl-(R,S)-allylglycine: Chiral scaffolds for drug discovery

All four diastereoisomers of 4-hydroxypipecolic acid were prepared in a form conveniently protected for drug discovery applications with the use of industrially scaleable methodology. Resolution of the racemic starting material using proprietary acylases followed by an acyliminium ion cyclisation gave diastereomeric mixtures of 4-formyloxypipecolic acid, which were differentiated using an enzyme-catalysed hydrolysis. The products were separated by partition, and by following a sequence of straightforward chemical steps, the individual stereoisomers of the protected 4-hydroxypipecolates were crystallized to optical purity in 100 g quantities.

Asymmetric synthesis of the four stereoisomers of 4-hydroxypipecolic acid

The asymmetric synthesis of all four stereoisomers of 4-hydroxypipecolic acid (1) from the polyfunctionalized chiral building blocks δ-amino β-keto esters (S(S),R)-(+)-5 or (R(S),S)-(-)-5 is described. Key steps in the synthesis are the stereoselective reductions of b-phenylpiperidine-2,4-dione (6) and N-sulfinyl δ-amino β-keto esters 5 to cis 4-hydroxy 2-piperidinone 7 and syn-δ-amino β-hydroxy ester 9, respectively. The only protecting/deprotecting group chemistry required is related to the oxidation step.