132488-71-2

Basic information

• Product Name: (+)-Vinylboronic acid pinanediol ester
• Synonyms: (+)-Vinylboronic acid pinanediol ester
• CAS NO: 132488-71-2
• Molecular Formula: C12H19BO2
• Molecular Weight: 206.09
• Product Categories: Alkenyl;Boronate Esters;Boronic Acids and Derivatives
• Mol File: 132488-71-2.mol

Chemical Properties

• Appearance: /
• Density: 1.002 g/mL at 25 °C
• Refractive Index: n20/D 1.479
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-Vinylboronic acid pinanediol ester(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Vinylboronic acid pinanediol ester(132488-71-2)
• EPA Substance Registry System: (+)-Vinylboronic acid pinanediol ester(132488-71-2)

Safety Data

• Hazardous Substances Data: 132488-71-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Vinylboronic acid pinanediol ester is used as a key intermediate in the synthesis of chiral allylboronate reagents. These reagents are crucial for the stereoselective allylboration of aldehydes, a reaction that plays a significant role in the development of various pharmaceutical compounds. The stereoselectivity of this process is essential for producing the desired enantiomers, which can have different biological activities and therapeutic effects.
Used in Chemical Synthesis:
In the field of chemical synthesis, (+)-Vinylboronic acid pinanediol ester is utilized as a versatile building block for the creation of more complex molecules. Its unique structure allows it to participate in various chemical reactions, such as cross-coupling and carbon-carbon bond formation, which are essential for the synthesis of a wide range of organic compounds.
Used in Research and Development:
(+)-Vinylboronic acid pinanediol ester is also employed in research and development laboratories, where it is used to study the properties and reactivity of boronic esters. This knowledge can be applied to the design and development of new synthetic routes, catalysts, and methodologies for the production of various chemical and pharmaceutical products.

Upstream product

• 230299-05-5 bis-(+)-pinanediolato diboron 
• 75927-49-0 pinacol vinylboronate 
• 6336-45-4 vinylboronic acid dibutyl ester 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 18680-27-8 pinanediol 
• 3677-80-3 dichlorovinylborane 
• 4363-34-2 vinylboronic acid 

Relevant articles and documents

Optisch aktive Vinylboronate

The comparative synthesis of optical active vinylboronates starting with (-)-2,3-pinanediol (5) or (+)-diethyltartrate (7) and dichlorovinylborane (4a), vinylboronic acid (4c), and dibutyl vinylboronate (4d) is described.A new method for the synthesis of dihalovinylboranes 4a, 4b is presented.

Transborylation of alkenylboranes with diboranes

Exchange of boryl moieties between alkenylboranes and diboron reagents has been postulated as a stereospecific cross-metathesis pathway with concomitant formation of mixed diboron reagents. DFT calculations propose a mechanism for the stereocontrolled C(sp2)-B/B′-B′ cross-metathesis with both symmetric and non-symmetric diboron reagents. This journal is

The preparation of optically active boronic ester substituted Δ2-isoxazolines

In this paper we report our recent results in the area of nitrile oxide cycloaddition to optically active vinylboronic esters to afford optically active boronic ester substituted Δ2-isoxazolines. In these studies, a number of optically active d

Pinanediol [α-(trimethylsilyl)allyl]boronate and related boronic esters

Homologation of (+)-pinanediol phenylboronate with [chloro(trimethylsilyl)methyl]lithium yielded (αS)-and (αR)-[α-(trimethylsilyl)benzyl]boronic esters in a 73:27 ratio, as shown by peroxidic deboronation to the known α-(trimethylsilyl)benzyl alcohol. Similar homologations of pinanediol vinyl, (Z)-1-propenyl, and isobutyl boronates were carried out, but the diastereoisomeric ratios were not determined. Reaction of the allylic α-trimethylsilyl boronic esters with aldehydes was studied. Pinanediol or pinacol 3-(trimethylsilyl)-1-propene-3-boronates yielded mainly (Z)-1-(trimethylsilyl)-1-alken-4-ols with aldehydes. Pinanediol (Z)-1-(trimethylsilyl)-2-butene-1-boronate with benzaldehyde yielded (E)-1-(trimethylsilyl)-3-methyl-4-phenylbut-1-en-4-ol with only 4% Z isomer. The stereochemical implications and utility of these reactions in synthesis are discussed. A brief investigation indicated that pinanediol α-trimethylsilyl boronic esters can be desilylated to boronic esters by tetrabutylammonium fluoride in moist THF.