178455-03-3

Basic information

• Product Name: (R)-BoroPhe-(+)-Pinanediol-HCl
• Synonyms: (R)-BoroPhe-(+)-Pinanediol-HCl;(R)-BoroPhe-(+)-Pinanediol-hydrochloride;(R)-Borophenylalanine-(+)-pinanediol-HCl;(R)-Borophenylalanine-(+)-pinanediola€￠HCl
• CAS NO: 178455-03-3
• Molecular Formula: C18H27BClNO2
• Molecular Weight: 335.67648
• Mol File: 178455-03-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-BoroPhe-(+)-Pinanediol-HCl(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-BoroPhe-(+)-Pinanediol-HCl(178455-03-3)
• EPA Substance Registry System: (R)-BoroPhe-(+)-Pinanediol-HCl(178455-03-3)

Safety Data

• Hazardous Substances Data: 178455-03-3(Hazardous Substances Data)

Usage

General Description

(R)-BoroPhe-(+)-Pinanediol-HCl is a chiral auxiliary molecule commonly used in asymmetric synthesis. It consists of a boron-containing group attached to a phenyl ring, as well as a pinanediol moiety. (R)-BoroPhe-(+)-Pinanediol-HCl is often utilized in the formation of chiral molecules, as the boron center allows for easy manipulation and control of stereochemistry during chemical reactions. The addition of a hydrogen chloride salt group to the molecule enhances its solubility and stability in various reaction conditions, making it a versatile and valuable tool in organic synthesis. Overall, (R)-BoroPhe-(+)-Pinanediol-HCl serves as a crucial building block for the creation of pharmaceuticals, agrochemicals, and other fine chemicals with high stereochemical purity.

Upstream product

• 78902-04-2 (+)-pinanediol (1R)-1-(N,N-bis(trimethylsilyl)amino)-2-phenylethaneboronate 
• 78902-03-1 1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester 
• 100-39-0 benzyl bromide 
• 87100-28-5 pinacol benzylboronate 
• 78922-83-5 (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester 
• 7647-01-0 hydrogenchloride 
• 7785-26-4 (-)-α-pinene 
• 20536-51-0 (+)-α-pinanediol 
• 88824-36-6 (-)-pinanediol phenylmethane-1-boronate 
• 88824-37-7 (R)-(1-chloro-2-phenylethyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester 

Downstream Products

• 1613134-43-2 1-[2-(2,3,4-trimethoxybenzoylamino)ethyl]-1H-[1,2,3]triazole-4-carboxylic acid [(R)-2-phenyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]dec-4-yl)ethyl]amide 
• 1613134-49-8 1-[2-(2-fluoro-4-trifluoromethylbenzoylamino)ethyl]-2H-[1,2,3]triazole-4-carboxylic acid [(R)-2-phenyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0²'⁶]dec-4-yl)ethyl]amide 
• 1613134-56-7 1-[2-(2-methoxy-4-trifluoromethylbenzoylamino)ethyl]-1H-[1,2,3]triazole-4-carboxylic acid [(R)-2-phenyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0²'⁶]dec-4-yl)ethyl]amide 

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 u

Structure-based development of (1-(3′-Mercaptopropanamido)methyl)boronic Acid Derived Broad-Spectrum, Dual-Action Inhibitors of Metallo- And Serine-β-lactamases

The emergence and spread of bacterial pathogens acquired metallo-β-lactamase (MBL) and serine-β-lactamase (SBL) medicated β-lactam resistance gives rise to an urgent need for the development of new dual-action MBL/SBL inhibitors. Application of a pharmacophore fusion strategy led to the identification of (2′S)-(1-(3′-mercapto-2′-methylpropanamido)methyl)boronic acid (MS01) as a new dual-action inhibitor, which manifests broad-spectrum inhibition to representative MBL/SBL enzymes, including the widespread VIM-2 and KPC-2. Guided by the VIM-2:MS01 and KPC-2:MS01 complex structures, further structural optimization yielded new, more potent dual-action inhibitors. Selectivity studies indicated that the inhibitors had no apparent inhibition to human angiotensin-converting enzyme-2 and showed selectivity across serine hydrolyases in E. coli and human HEK293T cells labeled by the activity-based probe TAMRA-FP. Moreover, the inhibitors displayed potentiation of meropenem efficacy against MBL- or SBL-positive clinical isolates without apparent cytotoxicity. This work will aid efforts to develop new types of clinically useful dual-action inhibitors targeting MBL/SBL enzymes.

Synthesis, in vitro and in vivo biological evaluation, and comprehensive understanding of structure-activity relationships of dipeptidyl boronic acid proteasome inhibitors constructed from β-amino acids

An extensive structure-activity relationship (SAR) study of 72 dipeptidyl boronic acid proteasome inhibitors constructed fromβ -amino acids is reported. SAR analysis revealed that bicyclic groups at the R1 position, 3-F substituents at the Rsu