40418-44-8

Usage

Uses

Used in Organic Synthesis:
POTASSIUM GLUTACONATE is used as a synthetic building block for the creation of a wide range of organic compounds. Its unique chemical properties allow it to be a valuable component in the synthesis of complex molecules, contributing to the development of new materials and pharmaceuticals.
Used in Pharmaceutical Industry:
POTASSIUM GLUTACONATE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its role in the development of new drugs is crucial, as it can be used to create molecules with specific therapeutic properties, potentially leading to the discovery of novel treatments for various diseases and conditions.
Used in Chemical Research:
POTASSIUM GLUTACONATE is also employed as a research tool in the field of chemistry. Its unique properties make it an interesting subject for study, allowing scientists to explore new reaction pathways and develop innovative synthetic strategies. This research can lead to a better understanding of chemical processes and the development of new methodologies in organic chemistry.

Upstream product

• 42824-16-8 pyridine-SO₃ complex 
• 4688-60-2 Zincke aldehyde 
• 26412-87-3 sulfur trioxide pyridine complex 

Downstream Products

• 1219005-87-4 (2E,4E)-5-(benzylamino)penta-2,4-dienal 
• 1033950-81-0 (2E,4E)-5-(dibenzylamino)penta-2,4-dienal 
• 1253523-07-7 (2E,4E)-5-(((S)-1-phenylethyl)amino)penta-2,4-dienal 
• 660430-03-5 neuroprotectin D1 
• 552830-51-0 Resolvin E₁ 
• 916888-47-6 resolvin D3 
• 1132757-67-5 (2E,4E)-5-{p-methoxybenzyl-[2-(3-indolyl)-ethyl]-amino}-penta-2,4-dienal 
• 71160-24-2 Leukotriene B 
• 83058-42-8 Methyl (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate 
• 1312756-65-2 (2R,6E,8E,10S)-12-methoxy-12-oxododeca-6,8-diene-2,10-diyl (2R,2'R)-bis(3,3,3-trifluoro-2-methoxy-2-phenylpropanoate) 
• 1352708-26-9 C₂₃H₂₄N₂OSe 
• 1338801-66-3 C₃₈H₄₂N₂O₅S₂ 

Relevant academic research and scientific papers

A pyridinium anionic ring-opening reaction applied to the stereodivergent syntheses of: Piperaceae natural products

A stereodivergent strategy has been devised to access the diene motif found in biologically active compounds from the Piperaceae family. Herein the first total syntheses of 2E,4E configured piperchabamide E (2) and its enantiomer (ent-2), as well as 2E,4Z configured scutifoliamide B (3), are narrated. The mainstay in the adopted approach is the gram-scale conversion of quaternized pyridine in a practical three-step sequence to access isomerically pure conjugated bromodiene esters 2E,4E8 and 2E,4Z9 by differential crystallization. Even though the developed oxidation protocol forms the basis of the entailed divergent strategy, the geometrical integrity of the involved bromodiene motive can be controlled by the choice of solvent. Thus, while oxidation of pure bromodienal 2E,4Z7 in methanol yields equal amounts of bromodiene esters 2E,4E8 and 2E,4Z9, only bromodiene ester 2E,4Z10 is formed in isopropanol. Subseqently, capitalizing on a stereoretentive Suzuki cross-coupling and direct amidation of the corresponding esters, the featured natural products can be accessed in five and six steps, respectively. The somewhat surprising (R)-configured amine portion, which has been assigned to piperchabamide E (2), is facilitated by a Curtius rearrangement. Following this, the actual amine portion is shown to be (S)-configured. This journal is

A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids

Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama-Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations of resolvin biology.

An efficient total synthesis of leukotriene B4

Lipid mediators have attracted great interest from scientists within the chemical, medicinal, and pharmaceutical research community. One such example is leukotriene B4 which has been the subject of many pharmacological studies. Herein, we report a convergent and stereoselective synthesis of this potent lipid mediator in 5% yield over 10 steps in the longest linear sequence from commercial starting materials. The key steps were a stereocontrolled acetate-aldol reaction with Nagao's chiral auxiliary and a Z-selective Boland reduction. All spectroscopic data were in agreement with those previously reported.

Stereoselective synthesis of protectin D1: A potent anti-inflammatory and proresolving lipid mediator

A convergent stereoselective synthesis of the potent anti-inflammatory, proresolving and neuroprotective lipid mediator protectin D1 (2) has been achieved in 15% yield over eight steps. The key features were a stereocontrolled Evans-aldol reaction with Nagao's chiral auxiliary and a highly selective Lindlar reduction of internal alkyne 23, allowing the sensitive conjugated E,E,Z-triene to be introduced late in the preparation of 2. The UV and LC/MS-MS data of synthetic protectin D1 (2) matched those obtained from endogenously produced material.

Stereoselective total synthesis of ieodomycin C

A concise stereoselective synthesis of the marine natural product ieodomycin C (3) has been achieved from commercially available pyridinium-1-sulfonate (8) in eight linear steps and 14% overall yield. The key synthetic steps included a B-alkyl Suzuki-Miyaura cross-coupling reaction and an Evans-Nagao acetate aldol reaction. The same synthetic sequence was used for preparing the enantiomer of ieodomycin C (3). Our efforts confirmed the structure of the antibacterial natural product 3.

Total synthesis of the lipid mediator PD1n-3 DPA: Configurational assignments and anti-inflammatory and pro-resolving actions

The polyunsaturated lipid mediator PD1n-3 DPA (5) was recently isolated from self-resolving inflammatory exudates of 5 and human macrophages. Herein, the first total synthesis of PD1n-3 DPA (5) is reported in 10 steps and 9% overall yield. These efforts, together with NMR data of its methyl ester 6, confirmed the structure of 5 to be (7Z,10R,11E,13E,15Z,17S,19Z)-10,17- dihydroxydocosa-7,11,13,15,19-pentaenoic acid. The proposed biosynthetic pathway, with the involvement of an epoxide intermediate, was supported by results from trapping experiments. In addition, LC-MS/MS data of the free acid 5, obtained from hydrolysis of the synthetic methyl ester 6, matched data for the endogenously produced biological material. The natural product PD1 n-3 DPA (5) demonstrated potent anti-inflammatory properties together with pro-resolving actions stimulating human macrophage phagocytosis and efferocytosis. These results contribute new knowledge on the n-3 DPA structure-function of the growing numbers of specialized pro-resolving lipid mediators and pathways.

Simple and convenient method for the synthesis of 2-substituted glutaconaldehyde salts and 2-substituted glutaconaldehyde derivatives

Convenient and scalable syntheses of 2-substituted glutaconaldehyde salts were accomplished from the corresponding pyridinium salts. Glutaconaldehyde salts were additionally converted into aminopentadienal derivatives.