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Usage

Uses

Used in Pharmaceutical Industry:
(R)-BoroPhe-(+)-Pinanediol is used as a chiral catalyst for the production of enantioenriched compounds, which are essential in the development of pharmaceuticals with improved efficacy and reduced side effects. Its ability to control stereochemistry in reactions is crucial for synthesizing complex molecules with specific biological activities.
Used in Agrochemical Industry:
In the agrochemical industry, (R)-BoroPhe-(+)-Pinanediol serves as a chiral catalyst for the synthesis of enantioselective agrochemicals, enhancing the effectiveness of these compounds and minimizing their environmental impact. The control of stereochemistry is vital for creating agrochemicals with targeted actions on pests or weeds, without affecting non-target organisms.
Used in Organic Chemistry Research:
(R)-BoroPhe-(+)-Pinanediol is used as a chiral ligand in research settings to explore new synthetic pathways and develop innovative methods for the formation of carbon-carbon and carbon-heteroatom bonds. Its application in organic chemistry research aids in the discovery of new reactions and the optimization of existing ones, contributing to the advancement of synthetic methodologies.
Used in Natural Product Synthesis:
(R)-BoroPhe-(+)-Pinanediol is employed as a chiral catalyst in the synthesis of natural products, which often possess complex stereochemistry. Its use in this field allows for the efficient and selective construction of these intricate molecules, facilitating the development of new drugs and other bioactive compounds derived from natural sources.
Used in the Synthesis of Biologically Active Molecules:
This chiral catalyst is also used in the synthesis of biologically active molecules, where stereochemistry plays a critical role in determining the molecule's activity and selectivity. (R)-BoroPhe-(+)-Pinanediol's ability to control the stereochemical outcome of reactions is essential for the development of molecules with specific biological targets and therapeutic potential.

Upstream product

• 18680-27-8 pinanediol 
• 1426585-64-9 (R_S)-N-(tert-butylsulfinyl)-2-phenylethanimine 
• 230299-05-5 bis-(+)-pinanediolato diboron 
• 1536530-77-4 C₂₂H₃₄BNO₃S 
• 78922-83-5 (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester 
• 78902-03-1 1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester 

Relevant academic research and scientific papers

Boronic acid derivatives

The present invention relates to boronic acid derivatives; the present invention provides compounds of formula (I) or pharmaceutically acceptable salts, solvates, polymorphs or isomers thereof, pharmaceutical compositions comprising these compounds, and uses of such compounds in the treatment of lmp7-related diseases.

Asymmetric synthesis of stable α-aminoboronic esters catalyzed by N-heterocylic carbene and copper(i) chloride

Bis(pinanediolato)diboron (B2pnd2) was used as the nucleophile instead of bis(pinacolato)diboron in the stereospecific synthesis of α-aminoboronic esters catalysed by a triazole-based N-hetereocyclic carbene (NHC) and Cu(i) chloride.

Design, synthesis, crystal structures, and antimicrobial activity of sulfonamide boronic acids as β-lactamase inhibitors

We investigated a series of sulfonamide boronic acids that resulted from the merging of two unrelated AmpC β-lactamase inhibitor series. The new boronic acids differed in the replacement of the canonical carboxamide, found in all penicillin and cephalosporin antibiotics, with a sulfonamide. Surprisingly, these sulfonamides had a highly distinct structure-activity relationship from the previously explored carboxamides, high ligand efficiencies (up to 0.91), and Ki values down to 25 nM and up to 23 times better for smaller analogues. Conversely, Ki values were 10-20 times worse for larger molecules than in the carboxamide congener series. X-ray crystal structures (1.6-1.8 A?) of AmpC with three of the new sulfonamides suggest that this altered structure-activity relationship results from the different geometry and polarity of the sulfonamide versus the carboxamide. The most potent inhibitor reversed β-lactamase-mediated resistance to third generation cephalosporins, lowering their minimum inhibitory concentrations up to 32-fold in cell culture.

Synthesis and Evaluation of Macrocyclic Transition State Analogue Inhibitors for α-Chymotrypsin

Lactams 1 and 2 are readily formed from acyclic precursors in the presence of trypsin and chymotrypsin, respectively, identifying the macrocyclic ring system as a potential motif for constrained transition state analogue inhibitors of the serine peptidases. Ketone 3 was synthesized and shown to be a modest inhibitor of chymotrypsin (Ki = 220 μM), albeit 4-fold more potent than the acyclic hydroxy acid 25 (Ki = 1.5 mM as a mixture of epimers). A precursor (31) to the amino boronic acid 4 was also prepared; although this derivative was a potent inhibitor of chymotrypsin (Ki = 130 nM) by virtue of the boronic acid moiety, it showed no advantage over the des-amino analogue 32 (Ki = 120 nM), which is not capable of cyclizing.