31456-71-0

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4,5-DIDEHYDROPIPECOLIC ACID is used as a key building block for the synthesis of various pharmaceutical compounds due to its unique structure and properties. Its potential pharmacological properties make it a valuable component in the development of new drugs and therapeutic agents.
Used in Biochemical Research:
In the field of biochemistry, (S)-4,5-DIDEHYDROPIPECOLIC ACID serves as an important research tool for studying the structure, function, and interactions of proteins and other biomolecules. Its unique configuration and properties allow scientists to gain insights into the mechanisms of various biological processes.
Used in Chiral Chemistry:
(S)-4,5-DIDEHYDROPIPECOLIC ACID is utilized as a chiral reference compound in the field of chiral chemistry. Its distinct "S" configuration makes it a useful standard for comparing and analyzing the properties of other chiral molecules, contributing to the advancement of stereoselective synthesis and asymmetric catalysis.
Used in Drug Development:
(S)-4,5-DIDEHYDROPIPECOLIC ACID is employed as a precursor in the development of novel drugs with potential therapeutic applications. Its unique structure and properties can be leveraged to design and synthesize new pharmaceutical agents that target specific biological pathways or receptors, leading to the discovery of innovative treatments for various diseases and conditions.

Upstream product

• 282527-09-7 methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate 
• 282527-06-4 methyl 2-[(1-benzyloxyallyl)-(4-nitrobenzenesulfonyl)amino]-(S)-pent-4-enoate 
• 282527-08-6 methyl (2S)-6-benzyloxy-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate 
• 305836-78-6 (2S)-1-(4-methylphenylsulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylic acid 
• 307304-57-0 (2S,4'S,5'R)-[(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)(1,3,4,6-tetrahydro-2-pyridinyl)]methanone 
• 141083-85-4 (S)-methyl 1,2,3,6-tetrahydropyridine-2-carboxylate 
• 919116-89-5 N-allyl-N-(1-benzyloxymethyl-3-hydroxy-propyl)-4-methyl-benzenesulfonamide 
• 919116-86-2 (2S)-N-allyl-N-(1-benzyloxymethyl-but-3-enyl)-4-methyl-benzenesulfonamide 
• 919116-87-3 (2S)-2-benzyloxymethyl-1-(4-methylphenylsulfonyl)-1,2,3,6-tetrahydropyridine 
• 919116-91-9 [1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-methanol 
• 919116-85-1 (2S)-N-allyl-N-[1-benzyloxymethyl-3-(t-butyldimethylsilanyloxy)propyl]-4-methylbenzenesulfonamide 
• 919116-90-8 N-allyl-N-(1-benzyloxymethyl-3-oxopropyl)-4-methylbenzenesulfonamide 

Downstream Products

• 76186-42-0 (S)-1-benzoyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid 
• 3105-95-1 pipecolinic acid 
• 273921-32-7 (2S)-N-benzoyl-2-piperidinecarboxylic acid 
• 417726-36-4 (S)-1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridine-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of pipecolic acid and baikiain

A straightforward synthesis of pipecolic acid and baikiain was achieved from trans-(2S,4R)-4-hydroxyproline via the key steps of regioselective Baeyer-Villiger reaction. and ring-closing metathesis.

Ring-closing metathesis of allylic O,O- and N,O-acetals

A variety of allylic O,O- and N,O-acetals were synthesized using a mild palladium-catalyzed coupling of an alcohol or sulfonamide with an alkyl or aryl 1,2-propadienyl ether. The resulting linear acetals were used for the synthesis of unsaturated rings via ring-closing metathesis, in which the acetal carbon-a precursor for oxycarbenium or N-sulfonyliminium ions, respectively-served as a reactive center for further introduction of functional groups. The products-unsaturated oxygen and nitrogen heterocyclic scaffolds - offer multiple opportunities for derivatization as illustrated with the synthesis of substituted dihydropyrans, chromenes, enantiopure tetrahydropyridines and an enantiomerically pure quinolizidine amino acid.

A ring-closing metathesis-mediated route to novel enantiopure conformationally restricted cyclic amino acids

A combination of palladium-catalysed N,O-acetal formation, ruthenium- catalysed ring-closing metathesis and N-sulfonyliminium ion-mediated C-C bond formation constitutes an efficient and versatile route to a set of enantiomerically pure 2,6-disubstituted unsaturated pipecolic acid derivatives.

1,5-dimethyl-4-phenylimidazolidin-2-one-derived iminic glycinimides: Useful new reagents for practical asymmetric synthesis of α-amino acids

New 1,5-dimethyl-4-phenylimidazolidin-2-one-derived acyclic chiral iminic glycine reagents have been prepared and diastereoselectively alkylated with activated alkyl halides and electrophilic olefins in the presence of lithium chloride under (a) strong bases (LHMDS, KOBu(t)) and low temperature (-78 °C,) conditions; (b) solid-liquid phase-transfer catalysis reaction (LiOH, TBAB, -20 °C) conditions, and (c) in the presence of organic bases (DBU, BEMP, TMG, -20 °C). In the case of dielectrophiles C- and N-alkylation takes place to afford heterocyclic derivatives. Hydrolysis of alkylated products has been carried out (a) in two-step procedures with LiOOH or LiOH followed by acidic hydrolysis or Dowex purification, (b) in one single-step under refluxing water to give the corresponding α-amino acid, (c) in the presence of DBU in methanol to provide N-protected α-amino acids methyl esters, or (d) by a protection-hydrolysis procedure to afford N-Boc-protected α-amino acids. The chiral imidazolidinone has generally been recovered in good yield. This methodology has been shown to be useful for the synthesis of acyclic and heterocyclic (S)- and (R)-α-amino acids.

Asymmetric synthesis of cyclic α-amino acids (-)-baikiain and (-)-4 methyleneproline from (S)-Boc-BMI

The enantiomerically pure glycine derivative tert-butyl (S)-2-(tert-butyl)-3-methyl-4-oxo-l-imidazolidinecarboxylate (Boc-BMI) reacts with (Z)-1,4-dichloro-2-butene and 3-chloro-2-(chloromethyl)-1-propene to give the bicyclic intermediates 5 and 6, respectively. These dialkylated systems are hydrolyzed to the corresponding heterocyclic a-amino acids (S)-baikiain (L-4,5-didehydropipecolic acid) and (S)-4-methylene proline which are obtained in 96 and 90% ee, respectively.