76110-79-7

Basic information

• Product Name: (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester
• Synonyms: (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester
• CAS NO: 76110-79-7
• Molecular Weight: 304.624
• Mol File: 76110-79-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester(76110-79-7)
• EPA Substance Registry System: (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester(76110-79-7)

Safety Data

• Hazardous Substances Data: 76110-79-7(Hazardous Substances Data)

Upstream product

• 75-09-2 dichloromethane 
• 76110-78-6 (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole 
• 18680-27-8 pinanediol 
• 2146-67-0 (dichloromethyl)lithium 
• 98-80-6 phenylboronic acid 

Downstream Products

• 76110-80-0 (+)-pinanediol (S)-1-phenylethane-1-boronate 
• 85922-61-8 (+)-pinanediol (αR)-α-chlorobenzylboronate 
• 497258-69-2 (+)-pinanediol (1R)-1-(2-thienylacetylamino)-1-phenylmethylboronate 
• 476334-31-3 (R)-(1-amino-1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester hydrochloride salt 

Relevant articles and documents

Mercapto-amide boronic acid derivative and application thereof as MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase) inhibitor

The invention provides a compound of a formula (I) shown in the specification, or a conformational isomer, or an optical isomer or a pharmaceutically acceptable salt thereof. The compound of the formula (I) shown in the specification has excellent broad-spectrum inhibitory activity on MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase), and can be used for preparing MBL and/or SBL inhibitors. Moreover, the compound disclosed by the invention has excellent antibacterial activity on multiple drug-resistant bacteria and is capable of reversing drug resistance of carbapenem drug-resistant bacteria, and the antibacterial effect of the compound is prior to those of positive control products such as L-captopril and tazobactam. The compound disclosed by the invention has very great potential in preparation of MBL/SBL dual inhibitors and medicines reversing drug resistance of carbapenem drug-resistance bacteria.

Nanomolar inhibitors of AmpC β-lactamase

β-lactamases are the most widespread resistance mechanism to β-lactam antibiotics, such as the penicillins and the cephalosporins. In an effort to combat these enzymes, a combination of stereoselective organic synthesis, enzymology, microbiology, and X-ra

(R,R)-2,3-butanediol as chiral directing group in the synthesis of (αS)-α-chloro boronic esters

(R,R)-2,3-Butanediol dichloromethane-boronate is a convenient reagent for attaching a chiral carbon to a Grignard or lithium reagent via zinc chloride catalyzed rearrangment of the intermediate borate complex, which yields (αS)-α-chloro boronic esters with 91-96% diastereoselectivity. The esters are easily hydrolyzed to crystalline boronic acids.