76110-78-6

Basic information

• Product Name: (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole
• Synonyms: (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole
• CAS NO: 76110-78-6
• Molecular Weight: 256.153
• Mol File: 76110-78-6.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole(76110-78-6)
• EPA Substance Registry System: (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole(76110-78-6)

Safety Data

• Hazardous Substances Data: 76110-78-6(Hazardous Substances Data)

Upstream product

• 18680-27-8 pinanediol 
• 98-80-6 phenylboronic acid 
• 1061181-00-7 (-)-4,5-dimethyl-2-phenyl[1.3.2]dioxaborolane 
• 1061180-99-1 (4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 7785-70-8 (+)-α-pinene 
• 1692-26-8 bis(propan-2-yl) phenylboronate 

Downstream Products

• 76110-79-7 (S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester 
• 85922-61-8 (+)-pinanediol (αR)-α-chlorobenzylboronate 
• 476334-31-3 (R)-(1-amino-1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester hydrochloride salt 
• 497258-69-2 (+)-pinanediol (1R)-1-(2-thienylacetylamino)-1-phenylmethylboronate 
• 78922-83-5 (1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester 
• 76110-80-0 (+)-pinanediol (S)-1-phenylethane-1-boronate 
• 78902-03-1 1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester 

Relevant articles and documents

Homologation of boronic esters with (dialkoxymethyl)lithiums. Asymmetric synthesis of α-alkoxy boronic esters

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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.

Design, synthesis and docking studies of novel dipeptidyl boronic acid proteasome inhibitors constructed from αα- and αβ-amino acids

A series of novel dipeptidyl boronic acid proteasome inhibitors constructed from αα- and αβ-amino acids were designed and synthesized. Their structures were elucidated by 1H NMR, 13C NMR, LC-MS and HRMS. These compounds were evaluated for their β5 subunit inhibitory activities of human proteasome. The results showed that dipeptidyl boronic acid inhibitors composed of αα-amino acids were as active as bortezomib. Interestingly, the activities of those derived from αβ-amino acids lost completely. Of all the inhibitors, compound 22 (IC50 = 4.82 nM) was the most potent for the inhibition of proteasome activity. Compound 22 was also the most active against three MM cell lines with IC50 values less than 5 nM in inhibiting cell growth assays. Molecular docking studies displayed that 22 fitted very well in the β5 subunit active pocket of proteasome.