Synonyms:Magnesium,bromovinyl- (7CI,8CI);Vinylmagnesium bromide (6CI);Bromovinylmagnesium;Ethenylmagnesium bromide;Norman reagent;
99% *data from raw suppliers
Vinylmagnesium Bromide (14% in Tetrahydrofuran, ca. 1mol/L) *data from reagent suppliers
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There total 4 articles about Vinylmagnesium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
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The research focuses on the enantio- and diastereodivergent synthetic route to various cyclitols, including derivatives of conduritol B, conduritol F, myo-inositol, and chiro-inositol, starting from D-xylose. The key experimental steps involve a ring-closing metathesis process and a diastereodivergent organometallic addition to a D-xylose-derived aldehyde. The study explores the stereochemical outcomes of vinylmetal additions to carbohydrate-derived aldehydes, utilizing different vinylmetal reagents, solvents, and chelating agents to control the stereoselectivity of the reaction. The reactants include D-xylose, vinylmagnesium bromide, vinyllithium, and various chelating salts, while analyses used to confirm the structures and stereochemistry of the synthesized compounds encompass NMR spectroscopy, optical rotation measurements, and high-resolution mass spectrometry. The research provides insights into the factors influencing the stereochemistry of organometallic addition reactions and offers a practical synthetic route to a diverse group of cyclitol derivatives with potential biological importance.
The research aimed to develop an efficient synthetic approach to the decalin unit, which is a key intermediate for the synthesis of compactin, a potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase and an effective hypocholesterolemic agent. The study focused on the microwave-accelerated intramolecular Diels-Alder reaction of substrates 5a-c, which were prepared from 3-ethoxy-2-cyclohexenone. The reaction involved the use of vinylmagnesium bromide, hydrochloric acid, lithium aluminum hydride, ethyl hydrogen malate, ethyl hydrogen fumarate, and BuLi with maleic anhydride. The researchers found that microwave irradiation significantly accelerated the reaction compared to conventional heating, leading to the formation of the desired exo adduct (7c) with high stereoselectivity. The resulting 7c was then converted to the decalin unit (2a) through a series of chemical reactions, thus accomplishing an effective synthesis of the decalin unit required for an approach to compactin.
The study focuses on the total synthesis of the methyl ester of L-660631, a novel natural product obtained from actinomyces fermentation, which is a potent inhibitor of cytosolic P-ketothiolase. The researchers aimed to develop a synthetic route that allows for the systematic replacement of the 1,3,5-hexatriyne subunit with more stable fragments to enhance the compound's stability while retaining its inhibitory activity. Key chemicals involved include cyclooctene, which serves as the starting material, and various reagents such as vinyl magnesium bromide, phenyl isocyanate, and lithium trifluoroborate organoalkyls. The study details the synthesis process, highlighting challenges such as the instability of concentrated L-660,631 and the difficulty in achieving selective addition reactions. The researchers employed techniques like asymmetric Sharpless kinetic resolution to set the stereochemistry at C.6 and C.9, and explored different methods for the oxidation and reduction steps to overcome the instability issues. The final product, L-660,631 methyl ester, was synthesized and found to be stable at room temperature, with future plans to evaluate its inhibitory activity against mammalian P-ketothiolase.
The research presents a concise and stereospecific synthesis of L-glycero-D-manno-Heptose (LD-Hepp) and its derivatives. The purpose of this study is to develop an efficient route for synthesizing LD-Hepp, a monosaccharide found in the core region of lipopolysaccharides of certain Gram-negative bacteria, which has potential applications in the synthesis of oligosaccharide building blocks for immunogenic substances. The researchers used readily available alcohol 1 as the starting material and employed Swern oxidation to convert it into aldehyde 2. This aldehyde was then condensed with vinylmagnesium bromide to form olefin 3, which was further transformed into LD-Hepp through oxidative cleavage of the double bond and reductive work-up. Key reagents used in the process include DMSO, (COCl)2, NEt3, NaBH4, OsO4, and NaIO4. The study concludes that the stereospecific vinylation of aldehyde 2 provides a new, easy route to LD-Hepp and its derivatives, which are of biological importance. The two-step transformation of the olefin into a hydroxymethyl group is compatible with various protecting groups and neighboring glycosidic linkages, making this method a valuable contribution to the synthesis of complex oligosaccharides.
The research focuses on the development of a common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl D-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B, two biologically significant compounds. The purpose of this study was to create an efficient method for synthesizing these compounds due to their importance in cell regulation, signal transduction, and antitumor, antiviral, and antifungal activities. The researchers achieved this by employing Grignard addition on N-benzyl sugar lactamine and Wittig olefination as key steps. Starting from D-ribose, an inexpensive sugar with the desired chirality, the synthesis involved a series of chemical reactions including the use of benzylamine, vinylmagnesium bromide, CbzCl (carbazole-9-yl chloride), ozone, NaBH4 (sodium borohydride), sodium hydride, tetra-n-butylammonium fluoride (TBAF), NaIO4 (sodium periodate), and various other reagents to protect and deprotect functional groups, as well as to introduce the necessary lipid chain and amino group. The successful synthesis of the target compounds was confirmed by comparing their physical properties with reported values, thus demonstrating a general strategy for the synthesis of these important sphingolipids and their derivatives.
The research describes a novel synthetic methodology for constructing spiro-fused isochroman-3-one derivatives, which are potentially useful as synthons for natural products such as Amaryllidaceae alkaloids. The study focuses on the tandem electrocyclic-sigmatropic reaction of benzocyclobutenylspirolactones, derived from 1-cyano-5-methoxybenzocyclobutene, to yield isochroman-3-one-4-spiro-1'-cycloalk-3'-enes in good yields. The process involves a series of chemical reactions, including alkylation, acid hydrolysis, basic hydrolysis, and acid treatment, utilizing chemicals such as LDA (lithium diisopropylamide), vinylmagnesium bromide, and various dioxolane derivatives. The conclusions of the research highlight the efficiency of this method in providing a unique route to合成spirocyclic compounds, with applications in the synthesis of Amaryllidaceae alkaloids currently underway.
The research explores various synthetic routes to produce 3-acetonyl- and 3-(2-oxoethyl)glutarates, which are important building blocks for synthesizing certain alkaloids and enantiopure piperidines. The study aims to develop a general, high-yield synthetic route that can be scaled up to multigram quantities. Key chemicals used include vinylmagnesium bromides, alkylidenemalonic esters, and reagents for specific transformations like LiAlH4 for reduction and TFA for desulfurization. The most successful route involves conjugate addition of vinylmagnesium bromide to an alkylidenemalonic ester, followed by bishomologation and reductive ozonolysis of a carbon–carbon double bond. This method achieved good overall yields and was scalable, making it a practical approach for synthesizing these compounds.
The study presents a chemoenzymatic asymmetric synthesis of (9S,12S,13S)- and (9S,12RS,13S)-pinellic acids, which are significant due to their adjuvant activity for influenza vaccines. The synthesis involves several key steps and chemicals. Initially, 1,9-nonanediol is monoprotected with para-methoxybenzyl chloride (PMBCl) to form compound 3, which is then oxidized with pyridinium chlorochromate (PCC) to yield aldehyde 4. The reaction of 4 with vinylmagnesium bromide produces allylic alcohol 5. A crucial step involves Novozyme 435-catalyzed acetylation of 5 with vinyl acetate, yielding (S)-acetate 6 and (R)-alcohol 5 with high enantiomeric excesses. Another significant component, (R)-cyclohexylideneglyceraldehyde 7, is reacted with CH3(CH2)4Li to form the anti-triol derivative 8, which is then protected with tert-butyldiphenylsilyl chloride (TPSCl) to form silyl derivative 9. The acetal function of 9 is removed to yield diol 10, which is cleaved with NaIO4 to form aldehyde 11. The reaction of 11 with vinylmagnesium bromide produces allylic alcohol 12. A cross-metathesis reaction between (S)-5 and 12, catalyzed by Grubbs 2nd generation catalyst, yields diol 13. Further steps involve silylation, oxidative removal of PMB protection, oxidation to form acid 16, and final desilylation to obtain the target pinellic acids. This method highlights the use of biocatalysis and chiral templates for efficient asymmetric synthesis, offering a simpler and more efficient route to these biologically active compounds.
The research explores the synthesis and properties of (E,E)-thiacyclodeca-4,7-diene (1) and its 3-methyl derivative (14) using D-mannitol as the starting material. The purpose of the study was to investigate the stereochemical and conformational behavior of these chiral compounds, which have interesting geometrical properties making them good candidates for such studies. The synthesis involved a series of stereospecific reactions, including the use of enantiomerically pure D-mannitol, (R,R)-cis-2,6-dioxabicyclo[3.3.0]octane (2), (R,R)-1,6-dibromohexane-3,4-diol (3), and various reagents like sodium sulfide, vinylmagnesium bromide, and t-BuOK. The key conclusion was that the synthesized compounds undergo rapid enantiomerization, with an energy barrier of approximately 11 kcal/mol, making them optically inactive. The study also revealed that the flipping motion of the sulfur atom has an energy barrier of around 6 kcal/mol. These findings highlight the dynamic behavior of these compounds and provide insights into their conformational motions.
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