52426-83-2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 73229-30-8 hepta-5,6-diene-1-ol 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 41323-59-5 5-Hydroxyhept-6-ene-1,5-diol 
• 124-63-0 methanesulfonyl chloride 
• 4117-10-6 6-hepten-1-ol 
• 1353881-76-1 C₉H₁₈O₃ 
• 2018-86-2 (E)-methyl 6-formylhex-2-enoate 
• 764-59-0 hex-5-en-1-al 
• 821-41-0 5-Hexen-1-ol 
• 99249-48-6 (E)-7-hydroxyhept-5-enal 
• 89794-62-7 (E)-Hept-2-ene-1,7-diol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 197219-29-7 (5E)-7-(tert-butyldiphenylsilyloxy)-5-hepten-1-ol 

Downstream Products

• 3857-14-5 2-ethyltetrahydropyran 
• 31502-17-7 non-5-en-1-ol 

Relevant academic research and scientific papers

PREPARATION D'α-ALCENYL-2 TETRAHYDROPYRANNES PAR CYCLISATION D'ALCOOLS δ-ALLENIQUES.

Four δ-allenic alcohols, prepared in several steps from dihydropyrane or from δ-valerolactone were cyclized with good yields to 2-alkenyl tetrahydropyranes using silver nitrate or mercuric trifluoroacetate.

Design, Synthesis, and Structural Analysis of Cladosporin-Based Inhibitors of Malaria Parasites

Here we have described a systematic structure activity relationship (SAR) of a set of compounds inspired from cladosporin, a tool compound that targets parasite (Plasmodium falciparum) lysyl tRNA synthetase (KRS). Four sets of analogues, synthesized based on point changes in the chemical scaffold of cladosporin and other logical modifications and hybridizations, were assessed using high throughput enzymatic and parasitic assays along with in vitro pharmacokinetics. Co-crystallization of the most potent compound in our series (CL-2) with PfKRS revealed its structural basis of enzymatic binding and potency. Further, we report that CL-2 has performed better than cladosporin in terms of metabolic stability. It thus represents a new lead for further optimization toward the development of antimalarial drugs. Collectively, along with a lead compound, the series offers insights on how even the slightest chemical modification might play an important role in enhancing or decreasing the potency of a chemical scaffold.

A chiral picolinic acid ligand, Cl-NAPH-PyCOOH, for CPRU-catalyzed dehydrative allylation: Design, synthesis, and properties

A CpRu/Br?nsted acid-combined catalyst, CpRu(II)/pico-linic acid (PyCOOH), acts as an efficient catalyst for the allyl protection/deprotection of alcohols. This discovery has resulted in the development of a new axially chiral ligand, Cl-Naph-PyCOOH (2a;

Enantioselective Iridium-Catalyzed Allylic Cyclizations

A method for the enantioselective synthesis of carbo- and heterocyclic ring systems enabled through the combination of Lewis acid activation and iridium-catalyzed allylic substitution is described. The reaction proceeds with branched, allylic alcohols and carbon nucleophiles as well as heteronucleophiles to give a diverse set of ring systems in good yields and with high enantioselectivities. The utility of the method is highlighted by the asymmetric syntheses of erythrococcamides A and B.

Stable yet reactive cationic gold catalysts with carbon based counterions

L-Au-[TsC(CN)2] are new cationic gold catalysts with a carbon based counterion, which are widely applicable for gold catalyzed reactions. For reactions which need highly reactive gold catalysts, a Lewis acid co-catalyst can be added to increase

Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation

The synthesis of chroman, isochroman, and pyran motifs has been accomplished via a combination of Pd(II)/bis-sulfoxide C-H activation and Lewis acid co-catalysis. A wide range of alcohols are found to be competent nucleophiles for the transformation under uniform conditions (catalyst, solvent, temperature). Mechanistic studies suggest that the reaction proceeds via initial C-H activation followed by a novel inner-sphere functionalization pathway. Consistent with this, the reaction shows reactivity trends orthogonal to those of traditional Pd(0)-catalyzed allylic substitutions.

Heterocycle synthesis based on allylic alcohol transposition using traceless trapping groups

Allylic alcohols undergo transposition reactions in the presence of Re 2O7 whereby the equilibrium can be dictated by trapping one isomer with a pendent electrophile. Additional ionization can occur when the trapping group is an aldehyde or ketone, thus leading to cyclic oxocarbenium ion formation. Terminating the process through bimolecular nucleophilic addition into the intermediate provides a versatile method for the synthesis of diverse oxygen-containing heterocycles. Understanding the relative rates of the steps in the sequence leads to the design of reactions which create multiple stereocenters with good to excellent levels of control.

The importance of hydrogen bonding to stereoselectivity and catalyst turnover in gold-catalyzed cyclization of monoallylic diols

Density functional calculations and experiment were used to examine the mechanism, reactivity, and origin of chirality transfer in monophosphine Au-catalyzed monoallylic diol cyclization reactions. The lowest energy pathway for cyclization involves a two-

A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers

The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl) di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the corresponding ethers. Additionally, it is reported that Reaxa QuadraPure MPA is an efficient scavenging reagent that halts the reaction progress.

Au-catalyzed cyclization of monoallylic diols

The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78° C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.