208521-42-0

Basic information

• Product Name: (R)-BoroAbu-(+)-Pinanediol
• Synonyms: (R)-BoroAbu-(+)-Pinanediol;(alphaR,3aS,4S,6S,7aR)-alpha-Ethylhexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole-2-methanamine
• CAS NO: 208521-42-0
• Molecular Formula: C13H24BNO2
• Molecular Weight: 237.15
• Mol File: 208521-42-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-BoroAbu-(+)-Pinanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-BoroAbu-(+)-Pinanediol(208521-42-0)
• EPA Substance Registry System: (R)-BoroAbu-(+)-Pinanediol(208521-42-0)

Safety Data

• Hazardous Substances Data: 208521-42-0(Hazardous Substances Data)

Usage

General Description

(R)-BoroAbu-(+)-Pinanediol is a chiral reagent used in organic synthesis as a building block for the preparation of various compounds. It consists of a boron atom attached to a pinanediol moiety, which has a unique stereochemistry due to the presence of a chiral carbon center. (R)-BoroAbu-(+)-Pinanediol is commonly used as a catalyst in asymmetric synthesis reactions to control the stereochemistry of the resulting products. Its ability to efficiently transfer chirality to other molecules makes it a valuable tool in the development of pharmaceuticals, agrochemicals, and other fine chemicals. Additionally, (R)-BoroAbu-(+)-Pinanediol can also be used for the preparation of chiral ligands for transition metal catalyzed reactions, making it a versatile and valuable reagent in synthetic chemistry.

Upstream product

• 319010-99-6 (1S,2S,6R,8S)-4-((S)-1-Chloro-propyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 

Downstream Products

• 437761-09-6 {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester 

Relevant articles and documents

Characterization of d-boroAla as a novel broad-spectrum antibacterial agent targeting d-Ala-d-Ala ligase

d-boroAla was previously characterized as an inhibitor of bacterial alanine racemase and d-Ala-d-Ala ligase enzymes (Biochemistry, 28, 1989, 3541). In this study, d-boroAla was identified and characterized as an antibacterial agent. d-boroAla has activity against both Gram-positive and Gram-negative organisms, with minimal inhibitory concentrations down to 8μg/mL. A structure-function study on the alkyl side chain (NH2-CHR-B(OR')2) revealed that d-boroAla is the most effective agent in a series including boroGly, d-boroHomoAla, and d-boroVal. l-boroAla was much less active, and N-acetylation completely abolished activity. An LC-MS/MS assay was used to demonstrate that d-boroAla exerts its antibacterial activity by inhibition of d-Ala-d-Ala ligase. d-boroAla is bactericidal at 1× minimal inhibitory concentration against Staphylococcus aureus and Bacillus subtilis, which each encode one copy of d-Ala-d-Ala ligase, and at 4× minimal inhibitory concentration against Escherichia coli and Salmonella enterica serovar Typhimurium, which each encode two copies of d-Ala-d-Ala ligase. d-boroAla demonstrated a frequency of resistance of 8×10-8 at 4× minimal inhibitory concentration in S. aureus. These results demonstrate that d-boroAla has promising antibacterial activity and could serve as the lead agent in a new class of d-Ala-d-Ala ligase targeted antibacterial agents. This study also demonstrates d-boroAla as a possible probe for d-Ala-d-Ala ligase function.