23580-75-8

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl piperidine-2,3-dicarboxylate is used as a precursor in the synthesis of pharmaceuticals for its ability to be incorporated into various drug molecules, contributing to the development of new medications.
Used in Agrochemical Industry:
It serves as a precursor in the synthesis of agrochemicals, playing a role in the creation of compounds that can be used in agricultural applications to protect crops and enhance yields.
Used in Organic Synthesis:
Dimethyl piperidine-2,3-dicarboxylate is used as a building block in the production of various fine chemicals, highlighting its versatility and importance as an intermediate in the chemical industry.

Upstream product

• 605-38-9 dimethyl 2,3-pyridinedicarboxylate 
• 67-56-1 methanol 
• 1253121-60-6 dimethyl 1,4,5,6-tetrahydropyridine-2,3-dicarboxylate 
• 149880-78-4 (2R,3S)-2,3-piperidinedicarboxylic acid dimethyl ester 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 

Downstream Products

• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 
• 79233-65-1 benzyl cis-3-(methoxycarbonyl)pipecolate 
• 79233-64-0 benzyl cis-1-<(tert-butyloxy)carbonyl>-3-(methoxycarbonyl)pipecolate 

Relevant academic research and scientific papers

Selective, Modular Probes for Thioredoxins Enabled by Rational Tuning of a Unique Disulfide Structure Motif

Specialized cellular networks of oxidoreductases coordinate the dithiol/disulfide-exchange reactions that control metabolism, protein regulation, and redox homeostasis. For probes to be selective for redox enzymes and effector proteins (nM to μM concentrations), they must also be able to resist non-specific triggering by the ca. 50 mM background of non-catalytic cellular monothiols. However, no such selective reduction-sensing systems have yet been established. Here, we used rational structural design to independently vary thermodynamic and kinetic aspects of disulfide stability, creating a series of unusual disulfide reduction trigger units designed for stability to monothiols. We integrated the motifs into modular series of fluorogenic probes that release and activate an arbitrary chemical cargo upon reduction, and compared their performance to that of the literature-known disulfides. The probes were comprehensively screened for biological stability and selectivity against a range of redox effector proteins and enzymes. This design process delivered the first disulfide probes with excellent stability to monothiols yet high selectivity for the key redox-Active protein effector, thioredoxin. We anticipate that further applications of these novel disulfide triggers will deliver unique probes targeting cellular thioredoxins. We also anticipate that further tuning following this design paradigm will enable redox probes for other important dithiol-manifold redox proteins, that will be useful in revealing the hitherto hidden dynamics of endogenous cellular redox systems.

Chiral synthesis of (S, S) - 2,8-diazabicyclononane method

The invention provides a method for chiral synthesis of (S,S)-2-8-diazabicyclo[4.3.0]nonane. A target product with a desired structure is prepared by using pyridine 2,3-diformate as a raw material and carrying out a four-step reaction comprising hydrogenation, resolution, aminolysis and reduction. According to the method, a synthetic route is simple and short, the step of resolution is carried out at an early stage, and reaction raw materials and reagents are saved; thus, production cost is reduced, and production efficiency is improved.

Preparation method of (S, S)-2, 8-diazabicyclo[4, 3, 0]nonane

The invention discloses a preparation method of (S, S)-2, 8-diazabicyclo[4, 3, 0]nonane and belongs to the field of the preparation method of a moxifloxacin intermediate. The preparation method comprises eight processes. A resolving process is carried out in initial of the preparation method, in the third process, an ester is resolved to form a chiral intermediate and then through a simple chemical reaction, the (S, S)-2, 8-diazabicyclo[4, 3, 0]nonane is prepared. The invention provides the preparation method utilizing an effective and economic synthesis route to prepare the high-chiral purity (S, S)-2, 8-diazabicyclo[4, 3, 0]nonane. The preparation method is free of an expensive resolving agent and greatly reduces a process cost. In the whole technology, the intermediate is not purified and the crude product can be directly used. The preparation method has simple processes and a high overall yield and can produce the product with chiral purity of 99%.

Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights

The catalytic kinetic resolution of cyclic amines with achiral N-heterocyclic carbenes and chiral hydroxamic acids has emerged as a promising method to obtain enantio-enriched amines with high selectivity factors. In this report, we describe the catalytic kinetic resolution of disubstituted piperdines with practical selectivity factors (s, up to 52) in which we uncovered an unexpected and pronounced conformational effect resulting in disparate reactivity and selectivity between the cis- and trans-substituted piperidine isomers. Detailed experimental and computational studies of the kinetic resolution of various disubstituted piperidines revealed a strong preference for the acylation of conformers in which the α-substituent occupies the axial position. This work provides further experimental and computational support for the concerted 7-member transition state model for acyl transfer reagents and expands the scope and functional group tolerance of the secondary amine kinetic resolution.

Efficient resolution of cis -(±)-dimethyl 1-acetylpiperidine-2,3-dicarboxylate with soluble Candida antarctica lipase B (CAL B)

(2S,3R)-Dimethyl 1-acetylpiperidine-2,3-dicarboxylate, a valuable intermediate for moxifloxacin, was prepared by CAL B catalyzed kinetic resolution of the racemic diester. The reaction has an optimum temperature of 45-50 °C and an optimum pH of 7.5. It follows typical Michaelis-Menten kinetics with Vmax,obsd = 0.061 ± 0.008 M/h/g, Km,obsd = 0.2 ± 0.045 M at 45°C. The reaction is highly enantioselective with an enantioselectivity E value of 80 at 45°C and pH 7.5. Preparative scale enzymatic resolution was carried out in 0.01 M sodium phosphate buffer, pH 7.5 at 45°C using a substrate loading of 8% (w/w) and a substrate-to-enzyme ratio of 2:1 (w/w). The reaction was complete in 16 h. The enantiomerically pure diester (ee >99%) is obtained in 47.5% yield (95% of theoretical). The unwanted hydrolyzed half ester (ee 87%) was easily converted back to racemic diester in 5 simple steps and 75% overall yield.

SYNTHESIS OF (4aS,7aS)-OCTAHYDRO-1H-PYRROLO[3,4-b]PYRIDINE

The present invention relates to the stereoselective synthesis of (4aS,7aS)-octahydro-1H-pyrrolo [3, 4-b]pyridine, as well as the conversion thereof, to give Moxifloxacin. Particularly, the present invention relates to a method for the synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3, 4-b]pyridine of formula (I) comprising : (a) the optical resolution by enzymatic hydrolysis of the intermediate dialkyl-1-alkylcarbonylpiperidine-2,3-dicarboxylate racemate of formula (II) to give, following isolation, the intermediate dialkyl-(2S,3R)-1-alkylcarbonyl-piperidine-2,3-dicarboxylate of formula (III) in which AIk is a straight or branched C1-C5 alkyl group; (b) the conversion of the intermediate (III) to (4aR,7aS)-1-alkylcarbonylhexahydrofuro[3, 4-b]pyridine-5,7-dione of formula (IV) in which AIk has the meanings set forth above; (c) the conversion of the intermediate (IV) to (4aS,7as)-octahydro-1H-pyrrolo[3, 4-b]pyridine of formula (I) with an optical purity above 99%.

Ureido-based peptidomimetic inhibitors of herpes simplex virus ribonucleotide reductase: An investigation of inhibitor bioactive conformation

We have been investigating peptidomimetic inhibitors of herpes simplex virus (HSV) ribonucleotide reductase (RR). These inhibitors bind to the HSV RR large subunit and consequently prevent subunit association and subsequent enzymatic activity. This report

HETEROCYCLIC-NMDA ANTAGONISTS

The present invention is directed to a class of 3-phosphono-piperidine and pyrrolidine derivatives and their use as NMDA antagonists.