5270-44-0

Upstream product

• 31996-72-2 (+/-)-2-oxabicyclo<4.2.0>octane-7-one 
• 154658-01-2 (E)-3-(4-Oxo-butoxy)-acrylic acid ethyl ester 
• 738604-53-0 6-methoxy-2,7-dioxabicyclo[4.3.0]nonan-2-one 
• 41324-11-2 1,4-dihydroxy-hex-5-ene 
• 201230-82-2 carbon monoxide 
• 864719-62-0 tert-butyl(dimethyl)silyl (2R,3R)-2-vinyltetrahydro-2H-pyran-3-yl ether 
• 864719-64-2 benzyl 2-((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate 
• 864719-63-1 2-[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]acetic acid 
• 918958-20-0 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran 
• 864719-91-5 [(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid benzyl ester 
• 864719-70-0 (2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-2-yl)acetate 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 864719-71-1 (2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate 
• 740845-32-3 [(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methanol 

Relevant academic research and scientific papers

Diastereofacial Selectivity in Intramolecular 1,4-Conjugate Additions: Conclusive Evidence for the Importance of Ground-State Conformations and the ?* Orbital Effect

The effects of the ground-state conformations and ?* orbital energies are both important to the diastereofacial selectivity of intramolecular 1,4 conjugate additions.

Microbiological transformations. 25. Enantioselective Baeyer-Villiger oxidation as a tool for the synthesis of enantiopure bicyclic furofuran and pyrofuran chirons

Several bicyclic [n.2.0] ketones were submitted to enzymatic Baeyer-Villiger oxidation and provided the corresponding regioisomeric lactones showing high enantiopurities. These products could be used as interesting chirons for the synthesis of various natural compounds. The absolute configurations of the obtained lactones were assigned using circular dichroism measurements.

Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans

In this study, we synthesized a series of enantiomerically pure (2R,3R)-disubstituted tetrahydropyrans with diverse functional groups. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW15

Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols

A palladium-catalyzed cascade carbonylative spirolactonization of hydroxycyclopropanols has been developed to efficiently synthesize oxaspirolactones common to many complex natural products of important therapeutic value. The mild reaction conditions, high atom economy, broad substrate scope, and scalability of this new method were highlighted in expedient total syntheses of the Turkish tobacco natural products α-levantanolide and α-levantenolide in two and four steps, respectively. The hydroxycyclopropanol substrates are readily available in one step via a Kulinkovich reaction of the corresponding lactones. Mechanistic studies utilizing high-resolution electrospray ionization mass spectrometry (ESI-MS) identified several key intermediates in the catalytic cycle, as well as those related to catalyst decomposition and competitive pathways.

The furan approach to oxacycles. Part 3: Stereoselective synthesis of 2,3-disubstituted tetrahydropyrans

Commercially available furan 1 was converted to 2,3-trans and 2,3-cis-disubstituted tetrahydropyrans 2 and 3 using a highly efficient route to oxacycles, based on the oxidation of the furan ring with singlet oxygen. Tetrahydropyrans 2 and 3 could be easil

Synthesis and cation complexation properties of new macrolides

The cis-2-alkyl-3-oxy-tetrahydropyran unit as a novel structure for the design and synthesis of a new type of ionophores with C2-symmetry is reported. The synthesis of seven different macrolides and a crown ether and their cation complexation p

Regiodivergent Baeyer-Villiger oxidation of fused ketone substrates by recombinant whole-cells expressing two monooxygenases from Brevibacterium

Microbial Baeyer-Villiger oxidations of fused bicyclic ketones with a cyclobutanone structural motif were investigated using recombinant Escherichia coli cells expressing two monooxygenases from Brevibacterium. In a kinetic resolution process fused ketones were transformed to regioisomeric lactones: 'normal' lactones were generated by migration of the more substituted carbon atom and 'abnormal' lactones resulted from migration of the less substituted carbon atom. The two Baeyer-Villigerases demonstrated a significantly different stereoselectivity for the regiodivergent biotransformation.

Diastereoselective radical cyclization of chiral β-alkoxyacrylates

(2R,3S)-3-Phenylcholestan-2-ol is a moderately effective chiral auxiliary in the radical cyclization of β-alkoxyacrylates.

Fused oxacycle synthesis via radical cyclization of -β alkoxyacrylates

β-Alkoxyacrylates are efficient radical acceptors in intramolecular addition of O-stannyl ketyls. This cyclization reaction can be applied reiteratively to form fused oxacycles.