36679-81-9

Upstream product

• 96-48-0 4-butanolide 
• 67-56-1 methanol 
• 143724-42-9 (rel)-(1S/1R,3S)-(tetrahydro-1-methoxyfuran-3-yl)methanol 
• 74106-34-6 acetic acid 5-oxo-tetrahydro-furan-3-ylmethyl ester 
• 541-47-9 3-Methylbutenoic acid 
• 61934-55-2 3-bromomethyl-2-butenolide 
• 75887-43-3 4-bromo-3-(bromomethyl)but-2-enoic acid 
• 81189-55-1 acetic acid 5-oxo-2,5-dihydrofuran-3-ylmethyl ester 
• 922500-91-2 ethyl 2-(oxetan-3-ylidene)acetate 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 
• 5472-38-8 diethyl 2-formylbutanedioate 
• 498-89-5 paraconic acid 
• 5204-92-2 ethyl 5-oxotetrahydro-3-furancarboxylate 
• 42927-61-7 methyl 5-methoxy-3-tetrahydrofuran-3-carboxylate 

Downstream Products

• 131072-60-1 4-(4-Methoxy-benzyloxy-methyl)-tetrahydrofuran-2-one 
• 28115-69-7 (+)-Epipinoresinol 
• 28115-69-7 (+/-)-piperitol methyl ether 
• 474622-91-8 4-benzyloxy-3-hydroxymethyl-N,N-dimethyl-butyramide 
• 530098-83-0 4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxymethyl-N,N-dimethyl-butyramide 
• 1309477-60-8 3-acetyl-4-((4-methoxybenzyloxy)methyl)dihydrofuran-2(3H)-one 
• 1309477-61-9 (E)-1-(4-(4-methoxybenzyloxymethyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl dimethyl phosphate 
• 1620754-39-3 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (5-oxotetrahydrofuran-3-yl)methyl carbonate 

Relevant academic research and scientific papers

Synthesis method of 4-hydroxymethyl-dihydro-furan-2(3H)-ketone

The invention belongs to the field of organic synthesis and drug synthesis, and particularly relates to a synthesis method of 4-hydroxymethyl-dihydro-furan-2(3H)-ketone. The synthesis method is carried out by a first step of mixing and stirring 3-oxetanone and ethoxyformyl methylidene triphenyl phosphorane solvent and obtaining an intermediate product 2-(oxetane-3-radical) ethyl acetate; a second step of hydrolyzing the intermediate product 2-(oxetane-3-radical) ethyl acetate through palladium carbon hydrogenation reduction under the alkali condition; meanwhile, completing rearrangement of reduction and oxygen heterocycles; obtaining 4-hydroxymethyl-dihydro-furan-2(3H)-ketone. The reaction condition of the synthesis method involved in the invention is easy to control, raw materials are low-price and easy to obtain; the operation and post treatment processes are simple; besides, the method is possessed of the industrial production value.

Synthesis and anti-retroviral activity of novel 5′-deoxy-5′,5′-difluoro-threosyl nucleoside phosphonic acid analogs

Novel 5′-deoxy-5′,5′-difluoro-threose purine phosphonic acid analogs were designed and synthesized from 2-propanone-1,3-diacetate. Direct displacement of the triflate intermediate 12 with diethyl (lithiodifluoromethyl) phosphonate provided the correspondi

Application of the palladium-catalysed norbornene-assisted catellani reaction towards the total synthesis of (+)-linoxepin and isolinoxepin

Our ongoing effort towards the development of highly selective transition-metal-catalysed C-H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/Pd IV-catalysed domino reaction, an aryl iodide, alkyl iodide and tert-butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The enantioselective total synthesis of the natural product (+)-linoxepin has been accomplished in eight steps starting from commercial materials. The key Pd-catalysed Catellani step served to combine aryl iodide, alkyl iodide and tert-butyl acrylate in a domino sequence. By tuning the final Heck reaction, both the natural product and its structural isomer were synthesized. Copyright

TRICYCLIC COMPOUNDS

The present invention provides a compound of formula I or a pharmaceutically acceptable salt thereof; and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

Total synthesis of (+)-linoxepin by utilizing the catellani reaction

Molecular intelligence: The structurally novel lignan (+)-linoxepin is synthesized in an eight-step sequence. The enantioselective synthesis features the palladium-catalyzed Catellani reaction as the key step. In this highly convergent multicomponent reaction, two new carbon-carbon bonds are formed, one of which results from a C-H bond functionalization. Copyright

Gas-phase fragmentation of γ-lactone derivatives by electrospray ionization tandem mass spectrometry

Fragmentation reactions of β-hydroxymethyl-, β-acetoxymethyl- and β-benzyloxymethyl-butenolides and the corresponding γ-butyrolactones were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) using collision-induced dissociation (CID). This study revealed that loss of H2O [M+H-18]+ is the main fragmentation process for β-hydroxymethylbutenolide (1) and β-hydroxymethyl-γ- butyrolactone (2). Loss of ketene ([M+H-42]+) is the major fragmentation process for protonated β-acetoxymethyl-γ-butyrolactone (4), but not for β-acetoxymethylbutenolide (3). The benzyl cation (m/z 91) is the major ion in the ESI-MS/MS spectra of β-benzyloxymethylbutenolide (5) and β-benzyloxymethyl-γ-butyrolactone (6). The different side chain at the β-position and the double bond presence afforded some product ions that can be important for the structural identification of each compound. The energetic aspects involved in the protonation and gas-phase fragmentation processes were interpreted on the basis of thermochemical data obtained by computational quantum chemistry. Copyright

Short and Efficient Synthesis of (±)-A-Factor

An efficient synthesis of (±)-A-factor via ring opening of electrophilic cyclopropane 2 with KOAc/AcOH, DMSO, as a key step is described.

Intramolecular inverse-electron-demand Diels-Alder reactions of imidazoles with 1,2,4-triazines: A new route to 1,2,3,4-tetrahydro-1,5-naphthyridines and related heterocycles

The intramolecular inverse-electron-demand Diels-Alder reaction between imidazoles and 1,2,4-triazines linked by a trimethylene tether from the imidazole N1 position to the triazine C3 proceed in excellent yields to produce 1,2,3,4-tetrahydro-1,5-naphthyridines. The reaction proceeds by a cycloaddition with subsequent loss of nitrogen, followed by a presumed stepwise loss of a nitrile. The analogous intramolecular cycloadditions employing a tetramethylene tether also proceeded to give 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines in acceptable yields. The reaction to produce the tetrahydro-1,5-naphthyridines can also be promoted with microwave irradiation.

Asymmetric Bayer-Villiger oxidation of cyclobutanones

The asymmetric Baeyer-Villiger oxidation of racemic cyclobutanones 1, 2, and 3 and a prochiral cyclobutanone 4 under Sharpless oxidation conditions resulted in the enantiomeric lactones 5 ee 34%, 6 ee 53%, 7 ee 75% and 8 40% ee respectively.

Asymmetric Synthesis of a Key Synthetic Precursor for (+)-Strigol and Sorgolactone

En-route to non-racemic iodomethyl butyrolactone 23g a number of stereoselective 1,4-additions and reductions have been studied.The only satisfactory approach involved baker's yeast reduction (21c->23c) as key step.