186906-12-7

Basic information

• Product Name: (R)-BoroPhe-(+)-Pinanediol
• Synonyms: (R)-BoroPhe-(+)-Pinanediol;(alphaR,3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-alpha-(phenylmethyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine;(R)-Borophenylalanine-(1S,2S,3R,5S)-(+)-2,3-pinanediol ester hydrochloride
• CAS NO: 186906-12-7
• Molecular Formula: C18H27BClNO2
• Molecular Weight: 335.67648
• Mol File: 186906-12-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 195-197℃
• Appearance: /
• Density: 1.10
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-BoroPhe-(+)-Pinanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-BoroPhe-(+)-Pinanediol(186906-12-7)
• EPA Substance Registry System: (R)-BoroPhe-(+)-Pinanediol(186906-12-7)

Safety Data

• Hazardous Substances Data: 186906-12-7(Hazardous Substances Data)

Usage

General Description

(R)-BoroPhe-(+)-Pinanediol is a chiral catalyst commonly used in organic chemistry reactions. It is a boron-containing compound that is derived from a pinanediol backbone and is used in asymmetric catalysis to promote enantioselective reactions. As a chiral ligand, it forms a complex with various metal ions, such as rhodium or palladium, and plays a crucial role in controlling the stereochemistry of the reaction. (R)-BoroPhe-(+)-Pinanediol has found applications in a wide range of synthetic transformations, including the formation of carbon-carbon and carbon-heteroatom bonds, making it a valuable tool in the pharmaceutical and agrochemical industries for the production of enantioenriched compounds. Its use has also been reported in the synthesis of natural products and biologically active molecules.

Upstream product

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

Relevant articles and documents

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.

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.