Category: tetrahydropyran

Expansion of first-in-class drug candidates that sequester toxic all-Trans-retinal and prevent light-induced retinal degeneration was written by Zhang, Jianye;Dong, Zhiqian;Mundla, Sreenivasa Reddy;Hu, X. Eric;Seibel, William;Papoian, Ruben;Palczewski, Krzysztof;Golczak, Marcin. And the article was included in Molecular Pharmacology in 2015.Product Details of 13417-49-7 This article mentions the following:

All-trans-retinal, a retinoid metabolite naturally produced upon photoreceptor light activation, is cytotoxic when present at elevated levels in the retina. To lower its toxicity, two exptl. validated methods have been developed involving inhibition of the retinoid cycle and sequestration of excess of all-trans-retinal by drugs containing a primary amine group. We identified the first-in-class drug candidates that transiently sequester this metabolite or slow down its production by inhibiting regeneration of the visual chromophore, 11-cis-retinal. Two enzymes are critical for retinoid recycling in the eye. Lecithin:retinol acyltransferase (LRAT) is the enzyme that traps vitamin A (all-trans-retinol) from the circulation and photoreceptor cells to produce the esterified substrate for retinoid isomerase (RPE65), which converts all-trans-retinyl ester into 11-cis-retinol. Here we investigated retinylamine and its derivatives to assess their inhibitor/substrate specificities for RPE65 and LRAT, mechanisms of action, potency, retention in the eye, and protection against acute light-induced retinal degeneration in mice. We correlated levels of visual cycle inhibition with retinal protective effects and outlined chem. boundaries for LRAT substrates and RPE65 inhibitors to obtain critical insights into therapeutic properties needed for retinal preservation. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Product Details of 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyran is a useful synthetic intermediate. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.Product Details of 13417-49-7

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Unstable crystalline phase in the D-glucose-water system was written by Dean, George R.. And the article was included in Carbohydrate Research in 1974.Application of 14431-43-7 This article mentions the following:

A crystalline phase of D-glucose was isolated from aqueous solution and found by optical-crystallog. study to be distinct from previously known forms of the sugar. Gas chromatog., polarimetric anal., and hydrate composition indicated that the phase may be a hydrated form of β-D-glucose. In solution the phase is metastable at 38-50°, and is transformed into stable α-D-glucose monohydrate at 32-38°. In the dry state at room temperature, the crystals change to pseudomorphs of the α monohydrate form. The secondary nucleation or “false grain” that often occurs when D-glucose monohydrate crystallizes is due largely to separation of this metastable phase, followed by transformation into small, thin crystals of the common form. Because of this behavior, the phase causes much difficulty in the com. production of crystalline D-glucose. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7Application of 14431-43-7).

(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Brønsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.Application of 14431-43-7

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Synthesis and Structure-Activity Relationships of 4-alkynyloxy Phenyl Sulfanyl, Sulfinyl, and Sulfonyl Alkyl Hydroxamates as Tumor Necrosis Factor-α Converting Enzyme and Matrix Metalloproteinase Inhibitors was written by Venkatesan, Aranapakam M.;Davis, Jamie M.;Grosu, George T.;Baker, Jannie;Zask, Arie;Levin, Jeremy I.;Ellingboe, John;Skotnicki, Jerauld S.;DiJoseph, John F.;Sung, Amy;Jin, Guixian;Xu, Weixin;McCarthy, Diane Joseph;Barone, Dauphine. And the article was included in Journal of Medicinal Chemistry in 2004.Formula: C9H16O3 This article mentions the following:

A series of 4-alkynyloxy Ph sulfanyl, sulfinyl and sulfonyl alkyl and piperidine-4-carboxylic acid hydroxamides were synthesized. Their structure-activity relationships, against tumor necrosis factor-α (TACE) and matrix metalloproteinase (MMP) inhibitor activities, are presented by investigating the oxidation state on sulfur and altering the P1′ substituent. Sulfonyl compounds prepared for this series carrying a 4-butynyloxy moiety were selective TACE inhibitors over the MMPs tested. Sulfinyl compounds prepared for this series showed a preference for a specific oxidation on sulfur. The selectivity over MMPs was also demonstrated in the sulfonyl series. The enhanced cellular activity was achieved upon incorporating a butynyloxy substituent in the piperidine series. 4-[[4-(2-Butynyloxy)phenyl]sulfonyl]-N-hydroxy-1-[(4-methoxyphenyl)methyl]-4-piperidinecarboxamide (I) and 4-[[4-(2-butynyloxy)phenyl]sulfonyl]-1-[(4-chlorophenyl)methyl]-N-hydroxy-4-piperidinecarboxamide were potent inhibitors of TNF-α release in the mouse at 100 mg/kg po. In the experiment, the researchers used many compounds, for example, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2Formula: C9H16O3).

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2) belongs to tetrahydropyran derivatives. Tetrahydropyrans and furans principally constitute as a central motif in diverse medicinally privileged molecules. There is large number of marine macrolide natural products that contain tetrahydropyran and tetrahydrofuran ring together. For instance, goniodomin A (actin targeting polyether), prorocentrolide (toxin halistatins), and percentotoxineFormula: C9H16O3

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Preparation of hydrated glucose by low-temperature crystallization was written by Arkhipovich, N. A.;Petrushevskii, V. V.;Bondar, E. G.. And the article was included in Sakharnaya Svekla in 1969.Quality Control of (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate This article mentions the following:

To obtain a good yield of glucose the initial upper crystallization temperature should be 35-8°. Over a period of 4.5 days, the yield of hydrated glucose from 100 g. syrup increases steadily, rising to 29 g., while the absolute crystallization rate falls, reaching 1.83 mg./m.2/min. at the end of the process. To obtain a good glucose yield combined with good massecuite quality, the syrup saturation should be the maximum possible consistent with the min. amount of “powder.” In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7Quality Control of (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate).

(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans and furans principally constitute as a central motif in diverse medicinally privileged molecules. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Quality Control of (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Spectroscopic and mechanistic studies of dioxouranium(VI) complexes derived from semi- and thiosemicarbazone ligands was written by Harek, Y.;Maki, A. K. T.;Mostafa, M. M.. And the article was included in International Journal of Chemistry in 1992.COA of Formula: C6H8O2 This article mentions the following:

The reaction between uranyl acetate dihydrate and some thiosemicarbazones in EtOH and/or in solid state is reported. The corresponding uranyl(VI) complexes with some semicarbazones were synthesized for the comparison between the effect of the carbonyl and thiocarbonyl groups towards the uranyl ion. All the complexes are characterized by elemental analyses, molar conductivities, spectra (IR, UV, NMR) and magnetic measurements. Also, mechanistic studies for the complexes with thiosemicarbazones in EtOH are explored. Also, the reaction of hard acid (UO₂²⁺) ion and the soft base as in case of thiosemicarbazone derivatives in the solid state is illustrated. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7COA of Formula: C6H8O2).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Brønsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.COA of Formula: C6H8O2

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Identification and persistence of 5,6-dihydro-2H-pyran-3-carboxaldehyde in aged aqueous acrolein media was written by Kissel, Charles L.;Bradly, Dakota L.;Shellhamer, Dale F.. And the article was included in Journal of Agricultural and Food Chemistry in 2021.Recommanded Product: 13417-49-7 This article mentions the following:

Acrolein hydrolysis byproducts are a part of good industrial stewardship practice. Aqueous acrolein is used worldwide as an industrial raw material, an herbicide, an oilfield biocide, a hydrogen sulfide scavenger, and a molluscicide. Industrial acrolein is obtained by the catalytic oxidation of propylene followed by aqueous absorption and then by distillations Generally, the fate of aqueous acrolein is described as occurring by hydrolysis, evaporation, absorption into the ground, and its consumption by the intended application purposes and conditions. Measurements of acrolein in water are normally confined to its loss. However, its byproducts are rarely discussed. In this study, an aged acrolein solution has been found to contain byproduct aldehydes, including the major soluble 5,6-dihydro-2H-pyran-3-carboxaldehyde. Despite acrolein’s facile hydrolysis degradation, this byproduct is surprisingly stable in aqueous media for at least 25 years at ambient temperatures The presence of this byproduct has been established by ¹H and ¹³C NMR, using DEPT, COSY, and HMBC, and UV spectroscopy at λ_max 229 nm in natural water systems. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Recommanded Product: 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyran is a useful synthetic intermediate. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. Pyran derivatives such as pyran flavonoids are biologically important. Monosaccharides containing six-membered rings are called pyranose.Recommanded Product: 13417-49-7

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics