900152-53-6

Usage

Uses

Used in Organic Synthesis:
3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic acid is used as a reagent for the formation of carbon-carbon and carbon-oxygen bonds in organic synthesis. Its protective t-butyldimethylsilyloxy group allows for mild deprotection conditions, making it a valuable building block in the synthesis of complex organic molecules.
Used in Cross-Coupling Reactions:
In the Pharmaceutical Industry, 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic acid is used as a reagent in cross-coupling reactions to form biaryl compounds. This is crucial for the synthesis of pharmaceuticals and other bioactive molecules that contain biaryl structures.
Used in Suzuki-Miyaura Couplings:
In the Chemical Industry, 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic acid is utilized as a reagent in Suzuki-Miyaura couplings, a type of carbon-carbon bond-forming reaction. This reaction is widely used in the synthesis of various organic compounds, including those with potential applications in materials science and medicinal chemistry.
Overall, 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic acid is a key component in the development of new chemical entities across various fields, including pharmaceuticals, agrochemicals, and materials science, due to its ability to facilitate the formation of complex molecular structures.

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 5419-55-6 Triisopropyl borate 
• 177329-71-4 5-Bromo-1-(tert-butyldimethylsilyloxy)-2-methoxybenzene 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 
• 37942-01-1 5-bromo-2-methoxyphenol 

Downstream Products

• 89701-84-8 volubolin 
• 10386-55-7 6-hydroxy-4-(3-hydroxy-4-methoxyphenyl)-7-methoxy-2H-1-benzopyran-2-one 
• 88126-45-8 3'-hydroxy-4',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one 
• 1123268-72-3 (E)-1,2-dihydro-4-[1-(3-hydroxy-4-methoxyphenyl)ethylidene]-6,7,8-trimethoxy-2-methylisoquinolin-3(4H)-one 
• 1123268-84-7 (E)-4-[1-(3-hydroxy-4-methoxyphenyl)ethylidene]-6,7,8-trimethoxy-1H-isochromen-3(4H)-one 
• 1453855-61-2 [(2R,3R,4R,5R,6R)-3,4,5-triacetoxy-6-[4-methoxy-3-(trifluoromethylsulfonyloxy)phenyl]tetrahydropyran-2-yl]methyl acetate 
• 1453855-76-9 [(2R,3S,4R,5S,6R)-3-acetoxy-4,5-dihydroxy-6-[4-methoxy-3-(trifluoromethylsulfonyloxy)phenyl]tetrahydropyran-2-yl]methyl acetate 

Relevant academic research and scientific papers

Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors

Recently, a series of selective human carboxylesterase inhibitors have been identified based upon the tanshinones, with biologically active molecules containing a 1,2-dione group as part of a naphthoquinone core. Unfortunately, the synthesis of such compounds is complex. Here we describe a novel method for the generation of 1,2-dione containing diterpenoids using a unified approach, by which boronic acids are joined to vinyl bromo-cyclohexene derivatives via Suzuki coupling, followed by electrocyclization and oxidation to the o-phenanthroquinones. This has allowed the construction of a panel of miltirone analogues containing an array of substituents (methyl, isopropyl, fluorine, methoxy) which have been used to develop preliminary SAR with the two human carboxylesterase isoforms. As a consequence, we have synthesized highly potent inhibitors of these enzymes (Ki 15 nM), that maintain the core tanshinone scaffold. Hence, we have developed a facile and reproducible method for the synthesis of abietane analogues that have resulted in a panel of miltirone derivatives that will be useful tool compounds to assess carboxylesterase biology.

TUBULIN BINDING AGENTS

The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.