17362-16-2

Upstream product

• 22002-36-4 2,6-bis(hydroxymethyl)-3,5-dimethylphenol 
• 76716-11-5 1,3-benzenedicarboxylic acid 2-hydroxy-4,6-dimethyl-1,3-dimethyl ester 
• 697-82-5 2,3,5-trimethylphenol 
• 42374-07-2 2-hydroxy-3,4,6-trimethylbenzaldehyde 
• 95-93-2 1,2,4,5-tetramethylbenzene 

Downstream Products

• 34059-79-5 Acetic acid 3-bromo-1,2,4,5-tetramethyl-6-oxo-cyclohexa-2,4-dienyl ester 
• 906623-20-9 1-bromo-4-(methoxymethoxy)-2,3,5,6-tetramethylbenzene 
• 1373551-63-3 methyl [(3S)-6-({4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',3',5',6'-tetramethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate 
• 1373551-64-4 [(3S)-6-({4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',3',5',6'-tetramethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid 
• 906623-25-4 4-[4-(methoxymethoxy)-2,3,5,6-tetramethylphenyl]pyridine 
• 906623-31-2 2,3,5,6-tetramethyl-4-(pyridin-4'-yl)phenol 

Relevant academic research and scientific papers

Pentamethylphenyl (Ph*) and Related Derivatives as Useful Acyl Protecting Groups for Organic Synthesis: A Preliminary Study

A study of acyl protecting groups derived from the Ph? motif is reported. While initial studies indicated that a variety of functional groups were not compatible with the Br 2-mediated cleavage conditions required to release the Ph? group, strategies involving the use of different reagents or a modification of Ph? itself (Ph*OH) were investigated to solve this problem.

Optimization of (2,3-dihydro-1-benzofuran-3-yl)acetic acids: Discovery of a non-free fatty acid-like, highly bioavailable G protein-coupled receptor 40/free fatty acid receptor 1 agonist as a glucose-dependent insulinotropic agent

G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) is a free fatty acid (FFA) receptor that mediates FFA-amplified glucose-stimulated insulin secretion in pancreatic β-cells. We previously identified (2,3-dihydro-1-benzofuran-3-yl)acetic acid derivative 2 as a candidate, but it had relatively high lipophilicity. Adding a polar functional group on 2 yielded several compounds with lower lipophilicity and little effect on caspase-3/7 activity at 30 μM (a marker of toxicity in human HepG2 hepatocytes). Three optimized compounds showed promising pharmacokinetic profiles with good in vivo effects. Of these, compound 16 had the lowest lipophilicity. Metabolic analysis of 16 showed a long-acting PK profile due to high resistance to β-oxidation. Oral administration of 16 significantly reduced plasma glucose excursion and increased insulin secretion during an OGTT in type 2 diabetic rats. Compound 16 (TAK-875) is being evaluated in human clinical trials for the treatment of type 2 diabetes.

Syntheses of sterically hindered pyridinium phenoxides as model compounds in nonlinear optics

Noncentrosymmetric molecules with a π-conjugated system and, among them, push-pull molecules such as pyridinium phenoxide, are a promising new class of materials for applications in optoelectronics due to their nonlinear optical (NLO) properties. Modelling studies have indicated that an increase in the twist angle between the two aromatic rings leads to an enhancement of the NLO properties. In order to confirm this feature experimentally, it was necessary to prepare a series of new hindered pyridinium phenoxides. Their efficient syntheses by Suzuki cross-coupling reactions are described herein. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.