Synonyms:3,4-dihydropyran
99% *data from raw suppliers
3,4-Dihydro-2H-pyran 98+% *data from reagent suppliers
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There total 47 articles about 3,4-Dihydro-2H-pyran 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:
Reference yield: 74.0%
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The research focuses on the synthesis of (+)-milbemycin p3, an important compound in the field of organic chemistry. The purpose of the study was to develop a more practical and cost-effective alternative synthesis method compared to the previously reported directed aldol approach. The new method employed the 3,4-dihydro-2H-pyran approach, which was highly convergent and utilized inexpensive chiral precursors. Key steps in the synthesis included nucleophilic scission of oxirane by vinyl alanate and metallated 3,4-dihydro-2H-pyran. The chemicals used in the process included phenylthiomethyl-lithium, aldehyde (5), vinyl alanate (4), acetylene (3), and metallated 3,4-dihydro-2H-pyran (15), among others. The conclusions of the research indicated that all reactions could be performed on a substantial scale, yielding products that were easily purified, making this approach more practical than the directed aldol method. The study also highlighted the importance of stereoselective synthesis of the spiroacetal moiety and the C(14)-C(15) trisubstituted double bond in the overall synthesis process.
The research explores a gold(I)-catalyzed method for the stereoselective synthesis of dihydropyrans from propargyl vinyl ethers. The purpose of this study is to develop an efficient and stereoselective approach to synthesize pyran-containing molecules, which are important in organic chemistry and natural product synthesis. The researchers discovered that by using a gold(I) complex, specifically [(Ph3PAu)3O]BF4, they could catalyze a tandem propargyl Claisen rearrangement and heterocyclization reaction. This process involves the formation of an oxocarbenium intermediate, which can be trapped by nucleophiles such as water or alcohols to form the desired dihydropyran products. The study demonstrated that various substituents at the alkyne terminus and the propargyl position were well-tolerated, and the reaction could also be used to synthesize spirocyclic compounds with excellent diastereocontrol. The conclusions drawn from this research highlight the potential of gold(I) catalysis for the stereoselective synthesis of complex pyran structures, with implications for the synthesis of natural products and other biologically active compounds.
The research focuses on the synthesis, characterization, and biological activity of 33 ring-substituted 6-benzylamino-9-tetrahydropyran-2-ylpurine (THPP) and 9-tetrahydrofuran-2-ylpurine (THFP) derivatives, aiming to enhance the specific biological functions of cytokinins used in plant micropropagation. The derivatives were prepared by condensing 6-chloropurine with 3,4-dihydro-2H-pyran or 2,3-dihydrofuran, followed by condensation with corresponding benzylamines. The compounds were characterized using elemental analyses, TLC, HPLC, melting point determinations, CI+ MS, and 1H NMR spectroscopy. The cytokinin activity was assessed through three bioassays: tobacco callus, wheat leaf senescence, and Amaranthus bioassay. Additionally, the susceptibility to enzyme degradation by cytokinin oxidase/dehydrogenase was studied, and the cytotoxicity against human cell lines was evaluated. The stability of selected compounds was also assessed at various pH levels using HPLC.
The study investigates the nickel-catalysed coupling of Grignard reagents with 6-alkyl-3,4-dihydro-2H-pyrans and acyclic enol ethers to produce trisubstituted alkenes with high stereoselectivity and retention of configuration. The key chemicals involved include various Grignard reagents (such as MeMgBr, PhMgBr, and BuMgBr), 6-alkyl-3,4-dihydro-2H-pyrans (like 6-pentyl-3,4-dihydro-2H-pyran and 6-isobutyl-3,4-dihydro-2H-pyran), and acyclic enol ethers. The study explores different methods for preparing the dihydropyrans and examines the scope and stereochemistry of the coupling reactions, finding that dihydropyrans are less reactive than dihydrofurans but still provide valuable routes to functionalized trisubstituted alkenes. The research also includes applications of the coupling reactions in the synthesis of natural product fragments, such as the aggregation pheromone of the square-necked grain beetle, a fragment of Premonensin B, and the polyketide fragment of Jaspamide.
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