1426957-69-8

Basic information

• Product Name: 3-(chloro(phenyl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine
• CAS NO: 1426957-69-8
• Molecular Weight: 329.634
• Mol File: 1426957-69-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-(chloro(phenyl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(chloro(phenyl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine(1426957-69-8)
• EPA Substance Registry System: 3-(chloro(phenyl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine(1426957-69-8)

Safety Data

• Hazardous Substances Data: 1426957-69-8(Hazardous Substances Data)

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 53710-18-2 3,5-diiodopyridine 
• 625-92-3 3,5-dibromopyridine 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1426957-63-2 3-(chloro(phenyl)methyl)-5-iodopyridine 
• 1426957-57-4 (5-iodopyridin-3-yl)(phenyl)methanol 

Downstream Products

• 1426957-75-6 3-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 1426957-54-1 3-benzyl-5-(4-(5-isobutylpyridin-3-yl)-2-isopropylphenyl)pyridine 
• 1426957-55-2 3-benzyl-5-(2-(sec-butyl)-4-(5-(naphthalen-2-ylmethyl)pyridin-3-yl)phenyl)pyridine 

Relevant articles and documents

A modular synthesis of teraryl-based α-helix mimetics, part 2: Synthesis of 5-pyridine boronic acid pinacol ester building blocks with amino acid side chains in 3-position

One of the most common protein-protein interactions (PPI) is the interaction of the α-helix of one protein with the surface of the second one. Terphenylic scaffolds are bioinspired motifs in the inhibition of PPIs and have been identified as suitable α-helix mimetics. One of the challenging aspects of this strategy is the poor solubility of terphenyls under physiological conditions. In the literature pyrrolopyrimidine-, pyrimidine- or pyridazine-based mimetics have been reported to show improved solubility. We present a new convergent strategy for the synthesis of linear pyridine-type teraryls based on a phenylic core unit. A general approach for the synthesis of 3,5-disubstituted pyridine-based boronic acid pinacol esters with amino acid side chains in the 3-position (representing Phe, Leu, Ile, Lys, Asp, Asn) is presented and exploits the functional group tolerance of the Knochel-Grignard reagents. The building blocks have been used in a convergent in situ two-step synthesis of teraryl α-helix mimetics. Tune in: The chemical orthogonality of Knochel's Grignard chemistry enables the synthesis of 3-substituted 5-pyridine-boronic esters with amino acid side chains, which can be used for convenient assembly of teraryl-based α-helix peptide mimetics by Suzuki coupling (see scheme; dppf=1,1′-bis(diphenylphosphino)ferrocene, DME= dimethoxyethane, Tf=trifluoromethanesulfonyl). Copyright