910132-85-3

Upstream product

• 341006-48-2 methyl 3,5-dimethyl-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate 
• 1663-39-4 tert-Butyl acrylate 
• 5471-81-8 methyl 4-iodo-3-methylbenzoate 
• 80-48-8 methyl p-toluene sulfonate 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 619-44-3 methyl 4-iodobenzoate 
• 34137-14-9 methyl 4-hydroxy-3,5-dimethylbenzoate 
• 4919-37-3 3,5-dimethyl-4-hydroxybenzoic acid 
• 10570-67-9 4-iodo-2,6-dimethylphenol 
• 576-26-1 2.6-dimethylphenol 

Downstream Products

• 910132-87-5 tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate 
• 910132-88-6 3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid 
• 910132-86-4 tert-butyl (E)-3-(2,6-dimethyl-4-carbamoylphenyl)acrylate 

Relevant academic research and scientific papers

Modular Dual-Tasked C-H Methylation via the Catellani Strategy

We report a dual-tasked methylation that is based on cooperative palladium/norbornene catalysis. Readily available (hetero)aryl halides (39 iodides and 4 bromides) and inexpensive MeOTs or trimethylphosphate are utilized as the substrates and methylating reagent, respectively. Six types of "ipso" terminations can modularly couple with this "ortho" C-H methylation to constitute a versatile methylation toolbox for preparing diversified methylated arenes. This toolbox features inexpensive methyl sources, excellent functional-group tolerance, simple reaction procedures, and scalability. Importantly, it can be uneventfully extended to isotope-labeled methylation by switching to the corresponding reagents CD3OTs or 13CH3OTs. Moreover, this toolbox can be applied to late-stage modification of biorelevant substrates with complete stereoretention. We believe these salient and practical features of our dual-tasked methylation toolbox will be welcomed by academic and industrial researchers.

Replacement of the N-terminal tyrosine residue in opioid peptides with 3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid (Dcp) results in novel opioid antagonists

3-(2,6-Dimethyl-4-carbamoylphenyl)propanoic acid (Dcp), a 2′,6′-dimethyltyrosine analogue containing a carbamoyl group in place of the hydroxyl function and lacking the amino group, was synthesized. The replacement of Tyr1 in an enkephalin analogue and in dynorphin A(1-11)-NH2 with Dcp resulted in the first opioid peptide-derived antagonists that do not contain a phenolic hydroxyl group at the 1-position residue. The cyclic peptide Dcp-c[D-Cys-Gly-Phe(pNO2)-D-Cys]NH 2 represents a novel, potent μ opioid antagonist.