23513-23-7

Basic information

• Product Name: cis-(±)-dimethyl piperidine-2,3-dicarboxylate
• CAS NO: 23513-23-7
• Molecular Weight: 201.222
• Mol File: 23513-23-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: cis-(±)-dimethyl piperidine-2,3-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: cis-(±)-dimethyl piperidine-2,3-dicarboxylate(23513-23-7)
• EPA Substance Registry System: cis-(±)-dimethyl piperidine-2,3-dicarboxylate(23513-23-7)

Safety Data

• Hazardous Substances Data: 23513-23-7(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 

Relevant articles and documents

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.

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.

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%.