122832-87-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(2-((tert-butoxycarbonyl)amino)-5-methoxyphenyl)boronic acid is used as a reagent and building block for the preparation of various pharmaceuticals. Its Boc-protected amine moiety allows for selective deprotection in the presence of other functional groups, making it a valuable component in the synthesis of complex drug molecules.
Used in Agrochemical Synthesis:
In the agrochemical industry, (2-((tert-butoxycarbonyl)amino)-5-methoxyphenyl)boronic acid is used as a reagent and building block for the preparation of various agrochemicals. Its versatility in chemical synthesis enables the development of new and improved agrochemicals with enhanced properties.
Used in Organic Material Synthesis:
(2-((tert-butoxycarbonyl)amino)-5-methoxyphenyl)boronic acid is used as a reagent and building block for the preparation of various organic materials. Its boronic acid functionality enables it to participate in Suzuki-Miyaura cross-coupling reactions, which are essential for the construction of complex organic molecules with potential applications in materials science.
Used in Chemical Synthesis Research:
In the field of chemical synthesis research, (2-((tert-butoxycarbonyl)amino)-5-methoxyphenyl)boronic acid is used as a versatile tool for exploring new synthetic methods and strategies. Its unique combination of Boc-protected amine and boronic acid functionalities allows researchers to investigate novel reactions and develop innovative approaches for the synthesis of complex organic molecules.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 104-94-9 4-methoxy-aniline 
• 121-43-7 Trimethyl borate 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 

Downstream Products

• 158818-68-9 (S)-2-(2-tert-Butoxycarbonylamino-5-methoxy-phenyl)-4-methoxy-6-methyl-cyclohexa-1,3-dienecarboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 177036-08-7 (S)-7,8-dihydro-6-[(1R,3R,4S)-p-menth-3-yloxy]-2,9-dimethoxy-7-methylphenanthridine 

Relevant academic research and scientific papers

An efficient synthesis of a lycobetaine-tortuosine analogue: A potent topoisomerase inhibitor

An efficient gram-scale synthesis that uses a Suzuki cross-coupling reaction to yield 5-methyl-2,9-dimethoxyphenanthridinium chloride, a lycobetaine-tortuosine analogue and potent topoisomerase inhibitor, is presented. Georg Thieme Verlag Stuttgart.

Harnessing Cascade Suzuki-Cyclization Reactions of Pyrazolo[3,4-b]pyridine for the Synthesis of Tetracyclic Fused Heteroaromatics

Numerous procedures have been described for the functionalization of pyrazolo[3,4-b]pyridine, mainly involving nucleophilic substitutions at the C-4 position or esterifications/amidations at the C-5 position. In this paper, we describe a robust, easy to implement protocol for the Suzuki cross-coupling reaction of chloroarene 2, followed by in-situ lactonization to provide chromenopyrazolopyridines. The extension of the scope of the reaction to fused naphthyridinones is also reported. This strategy gave access to 10 original pyrazolopyridine-containing tetracyclic compounds.

Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs

The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors.

Dynemicin analogs

Non-naturally occuring dynemicin analogs are provided, which are useful as DNA cleaving agents, cytotoxic agents, and/or anti-tumor compounds. Methods of making dynemicin analogs are also provided.

A convergent synthetic route to (+)-dynemicin a and analogs of wide structural variability

An enantioselective synthetic route to (+)-dynemicin A (1) is described that involves as the key and final step the Diels-Alder cycloaddition of the quinone imine 6 with the isobenzofuran 107 followed by an oxidative workup to provide (+)-1 in 40% yield. The synthetic route begins with the condensation of (-)-menthyl acetoacetate and trans-ethyl crotonate to form the crystalline cyclohexanedione 14, which is then transformed to the enantiomerically pure quinone imine 6 in 23 steps with an average yield of 85% and an overall yield of 2-3%. Key features of this sequence include the coupling of the enol triflate 11 and the arylboronic acid 10 (90%), the thermal deprotection/internal amidation of the coupling product 18 (84%), the use of 2-chloropyridine as an economical alternative to 2,6-di-tert-butylpyridine to promote the reaction of the quinolone 9 and triflic anhydride (85%), the highly stereoselective addition of the (Z)-enediyne 31 to the quinoline 61 (89%), intramolecular acetylide addition within the acetylenic ketone 66 (94%), and oxidation of the phenol 76 with iodosobenzene to afford the quinone imine precursor 77 in 89% yield. Both the quinone imine and isobenzofuran components of the final coupling reaction can be varied, thus providing an ideal route for the preparation of a wide variety of dynemicin analogs.