88557-53-3

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 80657-57-4 3-hydroxy-(2S)-methylpropionate 

Downstream Products

• 88557-54-4 (2R)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl 4-methylbenzenesulfonate 
• 88557-54-4 (S)-3-(tetrahydro-2-pyranyloxy)-2-methylpropyl p-toluenesulfonate 
• 110171-23-8 (S)-3-Methyl-4-<(tetrahydropyranyl)oxy>butanenitrile 
• 107692-03-5 (2R,3R)-2-methyl-1-(tetrahydropyran-2-yloxy)butan-2-ol benzyl ether 
• 96882-99-4 2(S)-methyl-3-phenylsulfonyl-1,5(S)-hexanediol-1-THP ether 
• 96882-99-4 2(R)-methyl-3-phenylsulfonyl-1,5(R)-hexanediol-1-THP ether 
• 96882-96-1 (S)-2-methyl-3-phenylthio-1-propanol THP ether 
• 96947-44-3 (2R)-2-methyl-1-(phenylsulfanyl)-3-(tetrahydropyran-2-yloxy)propane 
• 96882-97-2 (S)-2-methyl-1-(phenylsulfonyl)-3-(tetrahydropyranyloxy)propane 
• 96947-45-4 (R)-2-methyl-1-(phenylsulfonyl)-3-(tetrahydropyranyloxy)propane 
• 109687-73-2 5(S)-<(tert-butoxycarbonyl)amino>-2(R)-methyl-6-<4-(phenylmethoxy)phenyl>-1-<(2-tetrahydropyranyl)oxy>-trans-3-hexene 
• 165961-48-8 (4R)-<<5-(Tetrahydropyran-2-yloxy)-4-methyl-1-pentyl>oxy>(1,1-dimethylethyl)diphenylsilane 
• 65284-00-6 (R)-3-methyl-γ-butyrolactone 
• 88671-02-7 (R)-1-(benzyloxy)-2-methyl-3-[(tetrahydropyranyl)oxy]propan 

Relevant academic research and scientific papers

Oxysterols: 27-hydroxycholesterol and its radiolabeled analog

We describe a convenient and stereoselective route to the synthesis of 27-hydroxycholesterol. Also its radiolabeled analog, 22, 23 di [3H]-27-hydroxycholesterol with high specific radioactivity (55 Ci/mmol) was synthesized by this method. Julia

Total synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate, a major component of the sex pheromone of the stink bug: Edessa meditabunda

The male-produced sex pheromone of the stink bug Edessa meditabunda was previously identified as a mixture of the esters methyl 4,8,12-trimethylpentadecanoate (1) and methyl 4,8,12-trimethyltetradecanoate (2), produced in a ratio of 92 : 8, respectively.

Enantioselective Synthesis and Activity of All Diastereoisomers of (E)-Phytal, a Pheromone Component of the Moroccan Locust, Dociostaurus maroccanus

The Moroccan locust, Dociostaurus maroccanus (Thunberg, 1815) (Orthoptera: Acrididae), is a polyphagous pest capable of inflicting large losses in agriculture under favorable environmental and climatic conditions. Currently, control of the pest relies solely on the application of conventional insecticides that have negative effects on the environment and human safety. In the search for a more rational, environmentally acceptable approach for locust control, we have previously reported that (Z/E)-phytal (1) is a male-produced candidate sex pheromone of this acridid. This molecule, with two stereogenic centers at C-7 and C-11, has four different diastereomers along with the Z/E stereochemistry of the double bond at C-2. In this paper, we present for the first time the enantioselective synthesis of the four diastereomers of (E)-phytal and their electrophysiological and behavioral activity on males and females. Our results demonstrate that the (R,R)-phytal is the most active diastereomer in both assays, significantly attracting females in a double-choice Y olfactometer, and confirming the previous chromatographic assignment as component of the sex pheromone of the Moroccan locust.

SUBSTITUTED PYRAZOLOAZEPIN-4-ONES AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS

The present invention relates to novel substituted pyrazoloazepin-4-ones with phosphodiesterase inhibitory activity, as well as to their use as therapeutic agents the treatment of inflammatory diseases and conditions.

SUBSTITUTED PYRAZOLOAZEPIN-4-ONES AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS

The present invention relates to novel substituted pyrazoloazepin-4-ones with phosphodiesterase inhibitory activity, as well as to their use as therapeutic agents in the treatment of inflammatory diseases and conditions.

Strictly Alternating Sequences When Copolymerizing Racemic and Chiral Acetylene Monomers with an Organo-Rhodium Catalyst

A racemic mixture and two chiral monomers of 2-methyl-1-butyl propiolate, i.e., rac1, R1, and S1, were stereoregularly polymerized with a catalyst, [Rh(norbornadiene)Cl]2, in methanol at 40 °C to obtain the corresponding helical racemic and two chiral polymers, Prac1, PR1, and PS1, and a copolymer, Pco. The 1H and 13C NMR spectra of the racemic and chiral polymers differed, although the NMR spectra of their monomers were the same. The structures of the Pco copolymers with different chiral monomer ratios were analyzed using 1D and 2D NMR, optical rotation, circular dichroism (CD), UV-vis, and computational methods to elucidate the stereochemical effect of the chiral monomers together with the polymerization mechanism. The temperature dependence of 1H and 13C NMR spectra in line shape and intensity indicated that the helical main chain undergoes restricted rotation around the ester methylene bonds ?O-CH2- through a three-site jump exchange called an accordion-like helix oscillation (HELIOS). The energetically preferred structures of the helical-sense polymers PR1 or PS1 were simulated using the MMFF94 program. The dependence of the NMR spectral line shapes, optical rotations, and calculated structures on the monomer feed clearly indicated that the copolymers alternatively incorporate R1 and S1 to generate one-handed helical-sense chains. Based on these results, a polymerization mechanism is proposed, explaining a strictly alternating copolymerization that yields helical chains.

Toward a new palmerolide assembly strategy: Synthesis of C16-C24

Asymmetric synthesis of C16-C24 of palmerolide A is described, featuring convergent Negishi coupling, Singaram propargylation, and successful tactical maneuvering to address an unexpected allylic substitution reaction. Georg Thieme Verlag Stuttgart · New York.

Isolation, structural elucidation, and biosynthesis of 15-norlankamycin derivatives produced by a type-II thioesterase disruptant of Streptomyces rochei

Lankamycin, a 14-membered macrolide antibiotic, contains a 3-hydroxy-2-butyl side chain at C-13. To analyze the function of lkmE, which encodes type-II thioesterase in the lankamycin cluster, we carried out a gene disruption experiment. Disruption of lkmE

Hierarchical chiral expression from the nano- to mesoscale in synthetic supramolecular helical fibers of a nonamphiphilic C 3-symmetrical π-functional molecule

The controlled preparation of chiral structures is a contemporary challenge for supramolecular science because of the interesting properties that can arise from the resulting materials, and here we show that a synthetic nonamphiphilic C3 compound containing π-functional tetrathiafulvalene units can form this kind of object. We describe the synthesis, characterization, and self-assembly properties in solution and in the solid state of the enantiopure materials. Circular dichroism (CD) measurements show optical activity resulting from the presence of twisted stacks of preferential helicity and also reveal the critical importance of fiber nucleation in their formation. Molecular mechanics (MM) and molecular dynamics (MD) simulations combined with CD theoretical calculations demonstrate that the (S) enantiomer provides the (M) helix, which is more stable than the (P) helix for this enantiomer. This relationship is for the first time established in this family of C3 symmetric compounds. In addition, we show that introduction of the wrong enantiomer in a stack decreases the helical reversal barrier in a nonlinear manner, which very probably accounts for the absence of a majority rules effect. Mesoscopic chiral fibers, which show inverted helicity, i.e. (P) for the (S) enantiomer and (M) for the (R) one, have been obtained upon reprecipitation from dioxane and analyzed by optical and electronic microscopy. The fibers obtained with the racemic mixture present, as a remarkable feature, opposite homochiral domains within the same fiber, separated by points of helical reversal. Their formation can be explained through an oscillating crystallization mechanism. Although C3 symmetric disk-shaped molecules containing a central benzene core substituted in the 1,3,5 positions with 3,3′-diamido-2,2′-bipyridine based wedges have shown peculiar self-assembly properties for amphiphilic derivatives, the present result shows the benefits of reducing the nonfunctional part of the molecule, in our case with short chiral isopentyl chains. The research reported herein represents an important step toward the preparation of functional mesostructures with controlled helical architectures.

Stereochemistry of enacyloxins. Part 5: Synthesis of a C9′-C15′ fragment of enacyloxins, a series of antibiotics from Frateuria sp. W-315

The C9′-C15′ fragment of enacyloxins, a series of antibiotics isolated from Frateuria sp. W-315, was synthesized from diethyl D-tartrate. Copyright by Walter de Gruyter Berlin Boston.