62644-49-9

Usage

Uses

Used in Chemical Synthesis:
6-Acetoxy-2H-pyran-3(6H)-one is used as an intermediate in the preparation of 3-Methyl 2H-Furo[2,3-c]pyran-2-one (M305480), also known as "karrik". 6-Acetoxy-2H-pyran-3(6H)-one is found in smoke and is responsible for promoting seed germination, making it valuable in the agricultural industry for enhancing plant growth and development.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, due to its role as an intermediate in chemical synthesis, 6-Acetoxy-2H-pyran-3(6H)-one may also have potential applications in the pharmaceutical industry. It could be utilized in the development of new drugs or drug candidates, particularly those targeting specific biological pathways or molecular interactions.
Used in Agricultural Industry:
6-Acetoxy-2H-pyran-3(6H)-one is used as a synthetic intermediate for the production of compounds that promote seed germination. This application is particularly relevant in the agricultural industry, where enhancing seed germination rates and plant growth can lead to increased crop yields and more sustainable farming practices.

Upstream product

• 35436-57-8 6-hydroxy-3,6-dihydro-2H-pyran-3-one 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 98-00-0 (2-furyl)methyl alcohol 
• 75-36-5 acetyl chloride 
• 19969-71-2 2,5-dimethoxy-2-hydroxymethyl-2,5-dihydrofuran 

Downstream Products

• 88222-62-2 6-(2-Oxo-2-phenylethyl)-2H-pyran-3(6H)-on 
• 89189-01-5 6-endo-6-benzyloxy-8-oxabicyclo<3.2.1>oct-3-en-2-one 
• 74036-56-9 3,12-Dioxatricyclo<5.3.1.1.^2,6>dodeca-4,8-diene-10,11-dione 
• 71443-27-1 6-isopropoxy-2H-pyran-3(6H)-one 
• 71443-23-7 benzyl 2,3-dideoxy-α,β-DL-pent-2-enopyranosid-4-ulose 
• 71443-28-2 1-O-cyclohexyl-2,3-dideoxy-DL-pent-2-enopyrano-4-ulose 
• 581782-82-3 (R,S)-(+/-)-6-(3-methoxybenzyl)oxy-2H-pyran-3(6H)-one 

Relevant academic research and scientific papers

Intermolecular Regio- and Stereoselective Hetero-[5+2] Cycloaddition of Oxidopyrylium Ylides and Cyclic Imines

We have developed the first intermolecular hetero-[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio- and stereoselectivity. Surprisingly, divergent stereochemistry was observed depending on the substitution pattern of the oxidopyrylium ylide. This new reaction provides quick access to highly substituted nitrogen-containing seven-membered rings—azepanes. Notably, a broad range of oxidopyrylium ylides and cyclic imines participate in this novel hetero-[5+2] cycloaddition reaction and the cycloadducts can be readily transformed into the core skeletons of bioactive natural products. DFT calculations revealed that the cycloaddition proceeds through a stepwise pathway and the imine nitrogen atom serves as the nucleophile to initiate the cycloaddition.

Enantioselective 1,3-Dipolar [6+4] Cycloaddition of Pyrylium Ions and Fulvenes towards Cyclooctanoids

Organocatalytic enantioselective 1,3-dipolar [6+4] cycloadditions of pyrylium ion intermediates with fulvenes promoted by a chiral primary amine catalyst have been developed to proceed in moderate to good yields and high enantioselectivities. The resultant chiral bicyclo[6.3.0]undecane scaffold containing a transannular bridging ether is densely functionalised providing a rigid scaffold for further manipulations. Computational studies give important insights into the role of the primary amine catalyst. Analysis of the reaction shows that the catalytic reaction proceeds in a step-wise manner and rationalises the stereochemical outcome of the reaction. Several stereoselective complexity-generating transformations, facilitated by the diverse functional groups and transannular bridge, are presented, highlighting the versatility of the core towards a number of the cyclooctanoid natural products.

Design, Synthesis, and Phenotypic Profiling of Pyrano-Furo-Pyridone Pseudo Natural Products

Natural products (NPs) inspire the design and synthesis of novel biologically relevant chemical matter, for instance through biology-oriented synthesis (BIOS). However, BIOS is limited by the partial coverage of NP-like chemical space by the guiding NPs. The design and synthesis of “pseudo NPs” overcomes these limitations by combining NP-inspired strategies with fragment-based compound design through de novo combination of NP-derived fragments to unprecedented compound classes not accessible through biosynthesis. We describe the development and biological evaluation of pyrano-furo-pyridone (PFP) pseudo NPs, which combine pyridone- and dihydropyran NP fragments in three isomeric arrangements. Cheminformatic analysis indicates that the PFPs reside in an area of NP-like chemical space not covered by existing NPs but rather by drugs and related compounds. Phenotypic profiling in a target-agnostic “cell painting” assay revealed that PFPs induce formation of reactive oxygen species and are structurally novel inhibitors of mitochondrial complex I.

Expeditious metal-free access to functionalized polycyclic acetals under mild aqueous conditions

A facile approach for the synthesis of furopyrans and bicyclic bisacetals under mild aqueous conditions is described. This potentially green, diversity oriented approach involves cascade Michael addition and cycloacetalization of pyranones and 1,3-dicarbo

Discovery of inhibitors of the wnt and hedgehog signaling pathways through the catalytic enantioselective synthesis of an iridoid-inspired compound collection

Cousins you can count on: An iridoid-inspired compound collection was synthesized efficiently by the resolution of cyclic enones in an asymmetric cycloaddition with azomethine ylides. The collection contained novel potent inhibitors of the Wnt and Hedgehog signaling pathways. Copyright

beta-DIHYDROFURAN DERIVING COMPOUND, METHOD FOR PRODUCING beta-DIHYDROFURAN DERIVING COMPOUND OR beta-TETRAHYDROFURAN DERIVING COMPOUND, beta-GLYCOSIDE COMPOUND, METHOD FOR PRODUCING beta GLYCOSIDE COMPOUND, AND METHOD FOR PRODUCING 4'-ETHYNYL D4T AND ANALOGUE COMPOUNDS THEREOF

The invention provides a process for producing a β-dihydrofuran derivative represented by formula (1) or a β-tetrahydrofuran derivative represented by formula (4), characterized in that the process includes causing a dialkyl dicarbonate, a diaralkyl dicarbonate, or a halide to act on a diol compound represented by formula (2) or (3). The invention also provides a process for producing 4′-ethynyl-2′,3′-didehydro-3′-deoxythymidine or an analog thereof, the process including glycosylation and deprotection.

METHOD FOR PRODUCING 4'-ETHYNYL d4T

Disclosed is a method for mass-producing 4'-ethynyl d4T (4'-ethynyl-2',3'-didehydro-3'-deoxythymidine) by a simpler process at low cost. Specifically disclosed is a method for producing 4'-ethynyl d4T, which is characterized by comprising a step for introducing a triple bond-containing group into a furfuryl alcohol derivative or a levoglucosenone, by reacting the furfuryl alcohol derivative or levoglucosenone with a certain compound, and a step for reacting a compound represented by the formula (III), which is obtained by the aforementioned step, with thymine.

Cycloaddition of 3-oxidopyrylium: A novel route to functionalized cyclooctanoids from furans

We report a facile and efficient synthesis of highly functionalized cyclooctanoid derivatives by employing a dimerization reaction of 3-oxidopyrylium ylides. Different substituents are introduced on the dimer and the stereochemical outcome of the resultan

Synthesis of the seed germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-ones utilizing direct and regioselective Ti-crossed aldol addition

3-Methyl-2H-furo[2,3-c]pyran-2-ones 1 and 2, a unique and remarkable seed germination stimulant, and its analogue were synthesized using direct and regioselective Ti-crossed aldol addition between dihydro-2H-pyran-3(4H)-ones and methyl pyruvate as the key step, followed by furanone formation.

Practical, scalable, high-throughput approaches to η3- pyranyl and η3-pyridinyl organometallic enantiomeric scaffolds using the achmatowicz reaction

(Figure Presented) A unified strategy for the high-throughput synthesis of multigram quantities of the η3-oxopyranyl- and η3-oxopyridinylmolybdenum complexes TpMo(CO)2(η 3-oxopyranyl) and TpMo(CO)2(η3- oxopyridinyl) is described (Tp = hydridotrispyrazolylborato). The strategy uses the oxa- and aza-Achmatowicz reaction for the preparation of these organometallic enantiomeric scaffolds, in both racemic and high enantiopurity versions.