900152-53-6

Basic information

• Product Name: 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic
• Synonyms: 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic;3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic acid;3-(tert-butyldimethylsilyloxy)-4-methoxyphenylboronic acid
• CAS NO: 900152-53-6
• Molecular Formula: C₁₃H₂₃BO₄Si
• Molecular Weight: 282.22
• Mol File: 900152-53-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic(900152-53-6)
• EPA Substance Registry System: 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic(900152-53-6)

Safety Data

• Hazardous Substances Data: 900152-53-6(Hazardous Substances Data)

Usage

General Description

3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic acid is a boronic acid derivative that contains a phenyl ring with a methoxy group and a boronic acid moiety. It also features a t-butyldimethylsilyloxy group, which is commonly used as a protective group to stabilize reactive functionalities. 3-(t-Butyldimethylsilyloxy)-4-methoxyphenylboronic is often used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-oxygen bonds. It can be employed in cross-coupling reactions to form biaryl compounds, as well as in Suzuki-Miyaura couplings and other transformations. Additionally, its silicon-containing protecting group can be removed under mild conditions, making it a useful building block in the synthesis of complex organic molecules.

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

• 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 
• 1453855-75-8 [(2R,3S,4R,5S,6R)-3-acetoxy-4,5-dihydroxy-6-(3-hydroxy-4-methoxyphenyl)tetrahydropyran-2-yl]methyl acetate 
• 1453855-74-7 ((2R,3S,4R,5S,6R)-3-acetoxy-6-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl acetate 
• 1453855-42-9 C₂₉H₃₉NO₁₃ 
• 1453855-40-7 (2R,3S,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 

Relevant articles and documents

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.