Heterocyclic Building Blocks-Tetrahydropyran

Exploring the chemical space for freeze-drying excipients was written by Meng-Lund, Helena;Holm, Tobias Palle;Poso, Antti;Jorgensen, Lene;Rantanen, Jukka;Grohganz, Holger. And the article was included in International Journal of Pharmaceutics (Amsterdam, Netherlands) in 2019.Product Details of 14431-43-7 This article mentions the following:

Commonly, a limited number of generally accepted bulking agents and lyoprotectants are used for freeze-drying; predominantly mannitol, glycine, sucrose and trehalose. The purpose of this study was to combine a theor. approach using mol. descriptors with a large scale exptl. screening to evaluate the suitability of a broad range of excipients for freeze-drying. A large selection of sugars, polyols and amino acids was characterized by modulated differential scanning calorimetry (mDSC) and X-ray powder diffraction (XRPD) after well-plate based freeze-drying. The calculated mol. descriptors were investigated with both hierarchical cluster anal. and principal component anal. A clear clustering of the excipients according to the size-related and weight-related descriptors was observed; however other relevant descriptors could also be identified. From a practical perspective, a trend was observed with regard to a higher likelihood for amorphization and a higher glass transition temperature of the maximally freeze-concentrated solution with increasing mol. size. A translation of the mol. descriptors on pharmaceutical performance was more successful for lyoprotectants than for bulking agents. Addnl., in the course of the exptl. screening, several new potential bulking agents and lyoprotectants were identified. 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: 14431-43-7Product Details 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. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. Product Details of 14431-43-7

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

A new proof of structure of the cyclic dimers of α,β-ethylenic hydrocarbons was written by Dumas, Gerard;Rumpf, Paul. And the article was included in Compt. rend. in 1956.Recommanded Product: 13417-49-7 This article mentions the following:

Acrolein was dimerized in dilute HCl to 3-formyl-5,6-dihydro-α-pyran which gave a 78% yield of the corresponding acid, m. 83-4°, upon Ag₂O oxidation. Reduction of the acid with Raney Ni at 120 atm. and 100° gave tetrahydropyran-3-carboxylic acid (I), b₁₂ 136-7°; anilide, m. 131°. The dimer from the diene synthesis was reduced using Pt black, and the resulting formyltetrahydropyran treated with aqueous Ag₂O to give a tetrahydropyrancarboxylic acid (II), b₁₂ 126-7°; anilide, m. 122-3°. Ionization constants of II and I are 3.80 (20°) and 4.40 (18°), resp. These differences are taken as proof that the carbonyl group in the acrolein dimer from the diene synthesis is in the α-position so that II is tetrahydropyran-2-carboxylic acid. 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. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. Recommanded Product: 13417-49-7

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

Structure-Based Design of Selective β-Site Amyloid Precursor Protein Cleaving Enzyme 1 (BACE1) Inhibitors: Targeting the Flap to Gain Selectivity over BACE2 was written by Fujimoto, Kazuki;Matsuoka, Eriko;Asada, Naoya;Tadano, Genta;Yamamoto, Takahiko;Nakahara, Kenji;Fuchino, Kouki;Ito, Hisanori;Kanegawa, Naoki;Moechars, Diederik;Gijsen, Harrie J. M.;Kusakabe, Ken-ichi. And the article was included in Journal of Medicinal Chemistry in 2019.Safety of Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate This article mentions the following:

BACE1 inhibitors hold potential as agents in disease-modifying treatment for Alzheimer’s disease. BACE2 cleaves the melanocyte protein PMEL in pigment cells of the skin and eye, generating melanin pigments. This role of BACE2 implies that nonselective and chronic inhibition of BACE1 may cause side effects derived from BACE2. Herein, we describe the discovery of potent and selective BACE1 inhibitors using structure-based drug design. We targeted the flap region, where the shape and flexibility differ between these enzymes. Anal. of the cocrystal structures of an initial lead 8 prompted us to incorporate spirocycles followed by its fine-tuning, culminating in highly selective compounds 21 and 22. The structures of 22 bound to BACE1 and BACE2 revealed that a relatively high energetic penalty in the flap of the 22-bound BACE2 structure may cause a loss in BACE2 potency, thereby leading to its high selectivity. These findings and insights should contribute to responding to the challenges in exploring selective BACE1 inhibitors. In the experiment, the researchers used many compounds, for example, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2Safety of Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate).

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2) belongs to tetrahydropyran derivatives. In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Safety of Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate

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

Addition of aldehydes to activated double bonds. XXVIII. Preparations and reactions of alkoxy and acetoxy 2,5-diketones was written by Stetter, Hermann;Mohrmann, Karl Heinrich;Schlenker, Walter. And the article was included in Chemische Berichte in 1981.Related Products of 13417-49-7 This article mentions the following:

Reaction of ROCH₂CHO (R = Me, CHMe₂, Bu, CH₂Ph) with R¹COCH:CH₂ (R¹ = Me, Et, Ph) gave ROCH₂COCH₂CH₂COR¹, which were cyclized to I or reacted with R²NH₂ (R² = Me, Ph) to give the pyrroles II. RCOCH₂CH₂COCH₂OAc were obtained from RCHO and CH₂:CHCOCH₂OAc and were deacetylated to RCOCH₂CH₂COCH₂OH. Treatment of CH₂:CHCOR¹ with R³CHO (R³ = 2,3-dihydro-4H-pyran-2-yl, 2,3-dihydro-6H-pyran-2-yl) gave R³COCH₂CH₂COR¹ (R³ = tetrahydropyranyl). In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Related Products of 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. 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.Related Products of 13417-49-7

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

Gel permeation technique for characterizing chemically modified celluloses was written by Martin, Lawrence F.;Blouin, F. A.;Bertoniere, N. R.;Rowland, S. P.. And the article was included in Tappi 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:

Gel-permeation chromatog. is an effective method for obtaining quant. phys. measurements of changes produced in the structure of cellulose by chem. modification. The selection of stachyose, raffinose, maltose, and glucose as test solutes resulted in a simple linear relation between elution volume and hydrated mol. weight From this linear relation, extrapolation was made to the effective internal solvent volumes and limits of permeability of the samples. Values obtained were empirical measurements of the permeability of the cellulose samples, and the changes produced by chem. modifications agreed with the alteration of polymer structure. Cellulose crosslinked in the swollen state showed increased permeability because of its larger effective internal volume and limit of permeability. Crosslinking under conditions that minimize swelling increases the internal volume while causing a decrease in the limit of permeability. Monofunctional substitution increases the internal volume to the same extent as crosslinking in an unswollen state while increasing the limit of permeability. Microcrystalline wood cellulose had as large an internal volume as decrystd. cotton cellulose, but a much higher mol.-weight limit of permeability. 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 are useful synthons for biologically important compounds. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. 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

1,2-elimination of alcohol from homoallyl ethers under the influence of mixed metal bases was written by Margot, Christian;Rizzolio, Michele;Schlosser, Manfred. And the article was included in Tetrahedron in 1990.Application of 13417-49-7 This article mentions the following:

Lithium diisopropylamide in the presence of catalytic amounts of potassium tert-butoxide smoothly converts homoallyl or homobenzyl type ethers to dienes or styrenes. γ,δ-Unsaturated acetals give 1,3-dienyl ethers and 4-alkylidenetetrahydropyrans or dihydropyrans produce a variety of dienols. If there is a choice, the new double bond is formed with high trans selectivity while the configuration of existing double bonds is retained. The elimination mode is syn-periplanar and concerted, though E1cb like. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Application of 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Application of 13417-49-7

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

Derivatives of 5,6-dihydro-2H-pyran-3-carboxylic acid was written by Spreitzer, Helmut;Mueller, Petra;Buchbauer, Gerhard. And the article was included in Monatshefte fuer Chemie in 1990.Computed Properties of C6H8O2 This article mentions the following:

Some derivatives of 5,6-dihydro-2H-pyran-3-carboxaldehyde (I, R = CHO) and of its oxidation product, 5,6-dihydro-2H-pyran-3-carboxylic acid I (R = CO₂H), were prepared The aldehyde derivatives as well as amides and esters of I (R = CO₂H) were tested in an insecticidal/fungicidal/acaricidal screening program. The Me ester I (R = CO₂Me) shows a distinct knock down effect against the fruit fly Drosophila melanogaster. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Computed Properties of C6H8O2).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyran is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. 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.Computed Properties of C6H8O2

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

Carbon-13 NMR spectra of saturated heterocycles. XI. Tetrahydropyrans (oxanes) was written by Eliel, Ernest L.;Manoharan, Muthiah;Pietrusiewicz, K. Michal;Hargrave, Karl D.. And the article was included in Organic Magnetic Resonance in 1983.Reference of 13417-49-7 This article mentions the following:

The ¹³C NMR spectra of 62 oxanes (tetrahydropyrans) with and without Me substituents at various ring positions, some of them bearing in addition (or instead) Et, vinyl, ethynyl, carbomethoxy, and methylol substituents at C-2, have been recorded, and the 294 resulting chem. shifts have been correlated by multiple linear regression anal. Axial and equatorial α-, β-, γ-, δ-, gem– and vic-parameters for shifts caused by Me groups at all ring positions, and similar parameters for the other substituents at C-2, are reported. Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and exptl. shifts is excellent. ¹³C NMR spectra of a number of addnl. substituted tetrahydropyrans, and of 3,6-dihydro-2H-pyrans and 3,4-dihydro-2H-pyrans, are tabulated and discussed. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Reference of 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Reference of 13417-49-7

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

Flow Photo-Nazarov Reactions of 2-Furyl Vinyl Ketones: Cyclizing a Class of Traditionally Unreactive Heteroaromatic Enones was written by Ashley, William L.;Timpy, Evan L.;Coombs, Thomas C.. And the article was included in Journal of Organic Chemistry in 2018.Recommanded Product: 5,6-Dihydro-2H-pyran-3-carbaldehyde This article mentions the following:

Nazarov reactions of 2-furyl vinyl ketones and related heteroaromatic enones, to produce furan-fused cyclopentanones using a flow photochem. approach, are described. Compounds possessing this connectivity between heterocycle and ketone (2-furyl, 2-benzofuryl, 2-thiophene-yl, and 2-benzothiophene-yl) have traditionally proven difficult or impossible to cyclize with typical Bronsted and Lewis acid mediated methods. Using mild flow photochem. conditions and acetic acid (AcOH) or hexafluoroisopropanol (HFIP) as solvent, these compounds were found to cyclize in 45-97% yields, with typical UV exposure times of 3.4-6.8 min. In all cases, 2-furyl and 2-thiophene-yl enones cyclized, whereas 2-benzofuryl and 2-benzothiophene-yl enones exhibited divergent properties with reactivity patterns tied to the identity of the vinyl group. This report discloses the first photo-Nazarov reactions of tetrahydropyridine-substituted 2-furyl ketones, providing a direct approach to the corresponding fused heterocyclic motifs built around a central cyclopentanone. These motifs constitute the core structures of biol. active natural products, including the marine alkaloid nakadomarin A. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Recommanded Product: 5,6-Dihydro-2H-pyran-3-carbaldehyde).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Recommanded Product: 5,6-Dihydro-2H-pyran-3-carbaldehyde

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

Bayesian separation algorithm of THz spectral sources applied to D-glucose monohydrate dehydration kinetics was written by Sterczewski, L. A.;Grzelczak, M. P.;Nowak, K.;Szlachetko, B.;Plinski, E. F.. And the article was included in Chemical Physics Letters in 2016.Name: (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate This article mentions the following:

An estimation of the dehydration kinetics of monohydrated D-glucose with the use of the Bayesian spectral source separation algorithm is described. The dehydration experiment was probed with the terahertz time domain spectroscopy (THz-TDS). Contrary to the widely used peak-area method, our approach to the quant. anal. takes into account the full spectral information. The obtained concentration profiles at different temperatures were processed in order to measure the kinetics of the dehydration process. Our investigation shows that the proposed method may be used to estimate the evolution of concentration despite the overlapping peaks and multiple spectral sources in the observed spectra. 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: 14431-43-7Name: (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. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Name: (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate

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