70557-99-2

Usage

Uses

Used in Pharmaceutical Synthesis:
Iodomethylboronic acid, pinacol ester is used as a synthetic intermediate for the preparation of Taspase1 inhibitors and α-methylene-γ-butyrolactones. These compounds have potential applications in the development of therapeutic agents targeting specific enzymes and pathways involved in various diseases.
Used in Cancer Research:
In the field of cancer research, Iodomethylboronic acid, pinacol ester is used as a key component in the synthesis of α-methylene-γ-butyrolactones. These compounds have demonstrated the ability to suppress the growth of pancreatic carcinoma cells, making them promising candidates for the development of novel anticancer drugs.
Used in Organic Synthesis:
Iodomethylboronic acid, pinacol ester is employed as a reagent in various organic synthesis processes. Its ability to form stable boron-containing intermediates allows for the efficient construction of complex molecular architectures, which are essential in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 66080-23-7 4,4,5,5-tetramethyl-2-((phenylsulfanyl)methyl)-1,3,2-dioxaborolane 
• 75-11-6 diiodomethane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 31103-51-2 Jodmethyllithium 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 166330-03-6 pinacol (bromomethyl)boronate 
• 167967-38-6 diisopropyl (iodomethyl)boronate 
• 83622-42-8 2-(chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 7681-82-5 sodium iodide 

Downstream Products

• 281681-22-9 (E)-3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)propiophenone O-methyloxime 
• 134892-17-4 1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-one 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 364634-18-4 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethane 
• 1041203-01-3 potassium dimethyl 2-acetyl-2-methyl-3-(trifluoroborato)propanoate 
• 1041202-99-6 potassium methyl 2-phenylsulfonyl-3-(trifluoroborato)propanoate 
• 1041202-98-5 potassium 2,2-bis(phenylsulfonyl)ethyltrifluoroborate 
• 1041202-96-3 potassium 2-cyano-2-phenylsulfonylethyltrifluoroborate 
• 1041203-00-2 potassium dimethyl 2-acetyl-3-(trifluoroborato)propanoate 
• 1243333-14-3 (S)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)butanamide 
• 1243333-13-2 (R)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide 
• 1243333-15-4 (S)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)hexanamide 
• 1243333-16-5 (R)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,3-dimethyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)butanamide 
• 1396515-28-8 tert-butyl 2-methoxybenzyl{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl}carbamate 

Relevant academic research and scientific papers

PREPARATION OF HALOMETHANEBORONATES

A facile preparation of iodomethaneboronic esters is described.The key step utilizes a tin hydride reduction of dichloromethaneboronic esters.

Highly Diastereoselective Synthesis of Methylenecyclobutanes by Merging Boron-Homologation and Boron-Allylation Strategies

A highly diastereoselective synthesis of methylenecyclobutanes possessing a quaternary stereocenter is reported, in which boron homologation of an easily-generated cyclobutenylmetal species is performed, followed by an allylation reaction. Combining three

Methyl Radical Initiated Kharasch and Related Reactions

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).

Cyclopropanation of Terminal Alkenes through Sequential Atom-Transfer Radical Addition/1,3-Elimination

An operationally simple method to affect an atom-transfer radical addition of commercially available ICH2Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron-deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.

Total synthesis of virgatolide B

The first total synthesis of the benzannulated spiroketal virgatolide A is presented. Key features include sp3-sp2 Suzuki coupling of an enantiomerically enriched β-trifluoroboratoamide and an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction followed by global deprotection/cyclization with regioselectivity governed by internal hydrogen bonding.

Total synthesis of natural and non-natural δ 5,6δ12,13-jatrophane diterpenes and their evaluation as MDR modulators

We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

FLUOROBORON COMPOUND HAVING AROMATIC RING OR SALT THEREOF, AND PROCESS FOR PRODUCTION OF COMPOUND HAVING CYCLIC ETHER-FUSED AROMATIC RING BY USING THE SAME

Provided is a fluoroboron compound which is highly safe and stable and is capable of forming a cyclic ether-fused ring by the intramolecular alkoxymethylation reaction, or a salt thereof. The compound can be synthesized by the intramolecular alkoxymethylation reaction of a fluoroboron compound represented by the formula (I) or a salt thereof in the presence of a metal catalyst. (wherein the moiety represented by the formula represents an aromatic ring; L represents a substituent such as a halogen atom; R represents a substituted or unsubstituted alkylene group having 1 or 2 carbon atoms; and M represents an alkali metal cation or the like, with the proviso that L and -R-OCH2BF3M are respectively located on contiguous carbon atoms on the aromatic ring, or in the case of a fused aromatic ring, on two carbon atoms adjacent to one carbon at the fused position).

An improved synthesis route to functionalized 2-alkyn-1-ylboronates: Useful intermediates for the preparation of α-allenic alcohols

Functionalized 2-alkyn-1-ylboronates were successfully prepared in good yields by reacting various acyclic and cyclic (iodomethyl)boronates with various alkynyllithium salts. Amongst various (iodomethyl)boronates studied, 2-(iodomethyl)-1,3,2-dioxa-4,4,5,5-tetramethylborolane provided improved chemical yields of 2-alkyn-1-ylboronates with pyran- and triisopropylsilyl- substituted alkynyllithium salts. 2-Alkyn-1-ylboronate bearing an acid sensitive structure (pyran) was successfully synthesized which would be very difficult to achieve under previously reported reaction conditions. The exceptionally rapid rearrangement of the "ate" complex derived from the pinacol (iodomethyl)boronate, suppression of the side product formation, and the stability of the pinacol 2-alkyn-1-ylboronate are some of the notable merits of this protocol. This new procedure offers a simple and convenient alternative route to the existing methodologies, in terms of the milder reaction conditions, functional group compatibility, and the ease of the operation. The synthesis scope of this class of 2-alkyn-1-ylboronates was demonstrated by reacting the pinacol 2-alkyn-1-ylboronate with benzaldehyde, which yielded the α-allenic alcohol in good yield and regioselectivity.

Facile synthesis of highly functionalized ethyltrifluoroborates

(Formula Presented) Organotrifluoroborates are generating increased interest because of their ease of preparation and purification and indefinite shelf life. Herein we report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon - boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)2CH2 with potassium iodomethyltrifluoroborate resulted in di- and trisubstituted ethyltrifluoroborates in good to excellent yields.

Concise synthesis of ω-borono-α-amino acids

A short protocol for the practical scale synthesis of several ω-borono-α-amino acids is described via the alkylation of benzophenone glycinimines with various electrophiles. This journal is The Royal Society of Chemistry.