164513-32-0

Upstream product

• 131362-25-9 [3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 14472-14-1 4-bromo-3-methylphenol 
• 169315-83-7 (4-bromo-3-methylphenoxy)(tert-butyl)dimethylsilane 

Downstream Products

• 1030029-46-9 C₁₉H₃₂BrNO₃Si 
• 1438827-10-1 C₂₄H₄₅BO₃Si₂ 
• 1438825-50-3 tert-butyl(3-butyl-4-(dimethylsilyl)phenoxy)dimethylsilane 
• 478541-64-9 3-{2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid tert-butyl ester 

Relevant academic research and scientific papers

AROMATIC RING COMPOUND

Provided is an aromatic ring compound having a GPR40 agonist activity. A compound represented by the formula (I): wherein each symbol is as described in the DESCRIPTION, or a salt thereof has a GPR40 agonist activity, and is useful as an agent for the prophylaxis or treatment of diabetes and the like.

Regioselective electrophilic aromatic bromination: Theoretical analysis and experimental verification

Electrophilic aromatic bromination is the most common synthetic method used to prepare aryl bromides, which are very useful intermediates in organic synthesis. To understand the experimental results in electrophilic aromatic brominations, ab initio calculations are used here for a tentative analysis of the positional selectivity. The calculated results agree well with the corresponding experimental data, and the reliability of the resulting positional selectivity was verified by the corresponding experimental data.

Asymmetric total synthesis of (-)-quinocarcin

(-)-Quinocarcin (1) has been synthesized in a longest linear sequence of 22 steps from 3-hydroxybenzaldehyde in 16% overall yield. The Pictet-Spengler reaction of L-tert-butyl-2-bromo-5-hydroxy phenylalanate (17), synthesized according to Corey-Lygo's enantioselective alkylation process, with benzoxyacetaldehyde (12) under mild acidic conditions afforded 1,3-cis tetrahydroisoquinoline 20 as an only isolable stereomer in 91% yield. The diazabicycle[3,2,1]-octane ring system of 28 was constructed by a silver tetrafluoroborate-promoted intramolecular Mannich reaction using amino thioether as a latent N-acyliminium species and tethered silyl enol ether as a nucleophile. Using amino thioether instead of aminal as a precursor of N-acyliminium was of high importance to the success of this otherwise disfavored 5-endo-Trig cyclization. A Hf(OTf)4-catalyzed (0.1 equiv) transformation of aminal to amino thioether was uncovered in the course of this study, allowing the conversion of tricyclic aminal 24 to amino thioether 25 to be realized in high yield. From the bridged tetracyclic compound 28, a sequence of oxidation of aldehyde to acid, global deprotection under hydrogenolysis conditions, and one-pot partial reduction of lactam to aminal/oxazolidine formation completed the total synthesis of the pentacyclic (-)-quinocarcine.

Synthesis and evaluation of aminomethyl dihydrocinnamates as a new class of PPAR ligands

PPAR ligands with varied subtype selectivity have been synthesized using an achiral aminomethyl dihydrocinnamate template. Several compounds in this series have demonstrated potent plasma glucose and triglyceride lowering capability in rodent models of type 2 diabetes.