182617-55-6

Basic information

• Product Name: benzyl 4,4-dimethoxy-3-oxobutyrate
• Synonyms: benzyl 4,4-dimethoxy-3-oxobutyrate
• CAS NO: 182617-55-6
• Molecular Weight: 252.267
• Mol File: 182617-55-6.mol

Chemical Properties

• CAS DataBase Reference: benzyl 4,4-dimethoxy-3-oxobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 4,4-dimethoxy-3-oxobutyrate(182617-55-6)
• EPA Substance Registry System: benzyl 4,4-dimethoxy-3-oxobutyrate(182617-55-6)

Safety Data

• Hazardous Substances Data: 182617-55-6(Hazardous Substances Data)

Upstream product

• 6342-56-9 Pyruvic aldehyde dimethyl acetal 
• 3459-92-5 DBC 
• 89-91-8 Methyl dimethoxyacetate 
• 140-11-4 Benzyl acetate 
• 6956-50-9 ethyl 4,4-dimethoxy-3-oxo-butyrate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 228562-28-5 5-(2-cyanoethyl) 3-benzyl 4-(3-chlorophenyl)-2-dimethoxymethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 182617-59-0 (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid 
• 182617-58-9 (S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionic acid 

Relevant articles and documents

Synthetic, mechanistic, and biological interrogation of Ginkgo biloba chemical space en route to (-)-bilobalide

Here we interrogate the structurally dense (1.64 mcbits/?3) GABAA receptor antagonist bilobalide, intermediates en route to its synthesis, and related mechanistic questions. 13C isotope labeling identifies an unexpected bromine migration en route to an α-selective, catalytic asymmetric Reformatsky reaction, ruling out an asymmetric allylation pathway. Experiment and computation converge on the driving forces behind two surprising observations. First, an oxetane acetal persists in concentrated mineral acid (1.5 M DCl in THF-d8/D2O); its longevity is correlated to destabilizing steric clash between substituents upon ring-opening. Second, a regioselective oxidation of des-hydroxybilobalide is found to rely on lactone acidification through lonepair delocalization, which leads to extremely rapid intermolecular enolate equilibration. We also establish equivalent effects of (-)-bilobalide and the nonconvulsive sesquiterpene (-)-jiadifenolide on action potential-independent inhibitory currents at GABAergic synapses, using (+)-bilobalide as a negative control. The high information density of bilobalide distinguishes it from other scaffolds and may characterize natural product (NP) space more generally. Therefore, we also include a Python script to quickly (ca. 132 000 molecules/min) calculate information content (B?ttcher scores), which may prove helpful to identify important features of NP space.

Dihydropyridine derivative

Dihydropyridine derivatives of the following formula, analogs thereof and pharmaceutically acceptable salts thereof have an activity of selectively inhibiting the action of N-type calcium channel. They are used as remedies for various diseases relating to the N-type calcium channel. STR1

α-Dicarbonyls as 'non-charged' arginine-directed affinity labels. Novel synthetic routes to α-dicarbonyl analogs of the pp60(c-src) SH2 domain-targeted phosphopeptide Ac-Tyr(OPO3H2)-Glu-Glu-Ile-Glu

The phosphopeptide 1 is a potent inhibitor of pp60(c-src) SH2 domain mediated phosphoprotein interactions (IC50 ≤ 0.5 μM), but lacks cell permeability. The syntheses of its less charged analogs 2 and 3 are described, in which the arginine-binding phosphate group has been substituted with uncharged α-dicarbonyl moieties. The chemistry described here may be of general use for the synthesis of other α-dicarbonyl compounds.