Category: 20880-92-6

Vorcakova, Katarina published the artcileSynthesis and characterization of new inhibitors of cholinesterases based on N-phenylcarbamates: In vitro study of inhibitory effect, type of inhibition, lipophilicity and molecular docking, Formula: C12H20O6, the publication is Bioorganic Chemistry (2018), 280-289, database is CAplus and MEDLINE.

Based on current treatment of Alzheimer’s disease, where the carbamate inhibitor Rivastigmine is used, two series of carbamate derivatives were prepared: (i) N-phenylcarbamates with addnl. carbamate group and (ii) N-phenylcarbamates with monosaccharide moiety. All compounds were tested for the inhibitory effect on both of the cholinesterases, elec. eel acetylcholinesterase (eeAChE) and butyrylcholinesterase from equine serum (eqBChE) and the inhibitory activity (expressed as IC₅₀ values) was compared with that of the established drugs Galanthamine and Rivastigmine. The compounds with two carbamate groups revealed higher inhibitory efficiency on both cholinesterases in compared with monosaccharide derived carbamates and with Rivastigmine. The significant decrease of inhibitory efficiency on eqBChE (also for eeAChE but in less manner) was observed after deacetalization of monosaccharide. Moreover, the type of inhibitory mechanism of five chosen compounds was studied. It was found, that compounds with two carbamate groups act presumably via a mixed inhibitory mechanism and the compounds with monosaccharide moiety act as noncompetitive inhibitors. The lipophilicity of tested compounds was determined using partition coefficient Specific positions of the inhibitors in the binding sites of cholinesterases were determined using mol. modeling and the results indicate the importance of phenylcarbamate orientation in the catalytic gorges of both enzymes.

Bioorganic Chemistry published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C8H10S, Formula: C12H20O6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Yu, Wan-Lei published the artcileDehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen-Atom Transfer, and Cobalt Catalysis, Computed Properties of 20880-92-6, the publication is Angewandte Chemie, International Edition (2019), 58(32), 10941-10945, database is CAplus and MEDLINE.

A synergistic catalytic method combining photoredox catalysis, hydrogen-atom transfer, and proton-reduction catalysis for the dehydrogenative silylation of alkenes was developed. With this approach, a highly concise route to substituted allylsilanes has been achieved under very mild reaction conditions without using oxidants. This transformation features good to excellent yields, operational simplicity, and high atom economy. Based on control experiments, a possible reaction mechanism is proposed.

Angewandte Chemie, International Edition published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C18H16N2O6, Computed Properties of 20880-92-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhao, Jiacheng published the artcileCellular Uptake and Movement in 2D and 3D Multicellular Breast Cancer Models of Fructose-Based Cylindrical Micelles That Is Dependent on the Rod Length, Application In Synthesis of 20880-92-6, the publication is ACS Applied Materials & Interfaces (2016), 8(26), 16622-16630, database is CAplus and MEDLINE.

While the shape effect of nanoparticles on cellular uptake has been frequently studied, no consistent conclusions are available currently. The controversy mainly focuses on the cellular uptake of elongated (i.e., filaments or rod-like micelles) as compared to spherical (i.e., micelles and vesicles) nanoparticles. So far, there is no clear trend that proposes the superiority of spherical or nonspherical nanoparticles with conflicting reports available in the literature. One of the reasons is that these few reports available deal with nanoparticles of different shapes, surface chemistries, stabilities, and aspects ratios. Here, we investigated the effect of the aspect ratio of cylindrical micelles on the cellular uptake by breast cancer cell lines MCF-7 and MDA-MB-231. Cylindrical micelles, also coined rod-like micelles, of various length were prepared using fructose-based block copolymers poly(1-O-methacryloyl-β-D-fructopyranose)-b-poly(Me methacrylate). The critical water content, temperature, and stirring rate that trigger the morphol. transition from spheres to rods of various aspect ratios were identified, allowing the generation of different kinetically trapping morphologies. High shear force as they are found with high stirring rates was observed to inhibit the formation of long rods. Rod-like micelles with length of 500-2000 nm were subsequently investigated toward their ability to translocate in breast cancer cells and penetrate into MCF-7 multicellular spheroid models. It was found that shorter rods were taken up at a higher rate than longer rods.

ACS Applied Materials & Interfaces published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C19H21N3O3S, Application In Synthesis of 20880-92-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Yang, Liu published the artcileLight-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a Ni^II-Aryl Complex, Application of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, the publication is Angewandte Chemie, International Edition (2020), 59(31), 12714-12719, database is CAplus and MEDLINE.

A highly effective C-O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcs. is reported. Catalyzed by a Ni^II-aryl complex under long-wave UV (390-395 nm) irradiation in the presence of a soluble amine base without any addnl. photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcs., affording synthetically important ethers. Intramol. C-O coupling is also possible. The reaction appears to proceed via a Ni^I-Ni^III catalytic cycle.

Angewandte Chemie, International Edition published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C3H12Cl2N2, Application of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhou, Lin published the artcileTwo branched fructose modification improves tumor targeting delivery of liposomes to breast cancer in intro and in vivo, SDS of cas: 20880-92-6, the publication is Journal of Drug Delivery Science and Technology (2021), 102312, database is CAplus.

Breast cancer is the leading cause of cancer death for females and needs more specific treatments. D-fructose is a promising ligand targeting to glucose transporter 5 (GLUT5) on breast cancer cells, and single-branched fructose has been used for targeting nanoparticles. However, the impact of two-branched fructose on targeting delivery remains to be elucidated. In this study, we synthesized a two-branched fructose ligand, prepared fructose-decorating liposomes and evaluated them in vitro and in vivo. The results showed liposomes were approx. 102 nm-107 nm in size, with -3.19 mV to -3.61 mV zeta potential, and their encapsulation efficiency of paclitaxel (PTX) were 87% ∼ 91%. The liposomes decorated with two-branched fructose (Fru2-Lip) had the highest cellular uptake and cytotoxicity in 4T1 cells and MCF7 cells in vitro, and the strongest in vivo targeting delivery and accumulation in breast tumor sites, even compared with the liposomes decorated with two equivalent fructose. Further investigation of the mechanism underlying the increased targeting released the two-branched fructose had a 7.93 kcal/mol higher binding free energy to GLUT5, compared with the single-branched fructose. These results illustrated the two-branched fructose can significantly enhance the tumor-targeting of liposomes and supported the application of multi-branched ligands for the design of tumor-specific targeting delivery system.

Journal of Drug Delivery Science and Technology published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C3H9ClOS, SDS of cas: 20880-92-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhang, Tao published the artcileA directive Ni catalyst overrides conventional site selectivity in pyridine C-H alkenylation, Computed Properties of 20880-92-6, the publication is Nature Chemistry (2021), 13(12), 1207-1213, database is CAplus and MEDLINE.

Herein, application of bifunctional N-heterocyclic carbene-ligated Ni-Al catalyst in C3-H alkenylation of pyridines was described. This method overrode the intrinsic C2 and/or C4 selectivity, and provided a series of C3-alkenylated pyridines such as I in 43-99% yields and up to 98:2 C3 selectivity. This method not only allowed a variety of pyridine and heteroarene substrates to be used as the limiting reagent, but was also effective for the late-stage C3 alkenylation of diverse complex pyridine motifs in bioactive mols.

Nature Chemistry published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C25H29N9O3, Computed Properties of 20880-92-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Shen, Haigen published the artcileTrifluoromethylation of alkyl radicals in aqueous solution, HPLC of Formula: 20880-92-6, the publication is Journal of the American Chemical Society (2017), 139(29), 9843-9846, database is CAplus and MEDLINE.

The copper-mediated trifluoromethylation of alkyl radicals is described. The combination of Et₃SiH and K₂S₂O₈ initiates the radical reactions of alkyl bromides or iodides with BPyCu(CF₃)₃ (BPy = 2,2′-bipyridine) in aqueous acetone at room temperature to afford the corresponding trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl halides and exhibits wide functional group compatibility. A mechanism involving trifluoromethyl group transfer from Cu(II)-CF₃ intermediates to alkyl radicals is proposed.

Journal of the American Chemical Society published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H10O4S, HPLC of Formula: 20880-92-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Xu, Chunfa published the artcileA Multistage Halogen Bond Catalyzed Strain-Release Glycosylation Unravels New Hedgehog Signaling Inhibitors, COA of Formula: C12H20O6, the publication is Journal of the American Chemical Society (2019), 141(13), 5381-5391, database is CAplus and MEDLINE.

Halogen bonding (XB) has recently emerged as a promising noncovalent activation mode that can be employed in catalysis. However, methodologies utilizing XB remain rare, and the hydrogen-bonding (HB) catalysis congeners are more widespread in comparison. Herein, we demonstrate a remarkable case whereby employment of XB catalysis in strain-release glycosylation generates O,N-glycosides in excellent anomeric selectivity exceeding HB activation. Deeper investigation unraveled XB catalyst dependencies on multiple stages of the mechanism and a hitherto unknown XB-glycosyl acceptor activation. We present a proof of concept to interrogate sp³-rich glycosidic chem. space for novel biol. activity, by integrating XB-catalyzed construction of a glycosidic compound collection, and evaluating these analogs via cell-based phenotypic screens. We show that XB-catalyzed strain-release glycosylation defines a new class of glycosides that inhibit the hedgehog signaling pathway through a nonsmoothened mode of action, opening new opportunities to combat acquired cancer resistance.

Journal of the American Chemical Society published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C4H5NS2, COA of Formula: C12H20O6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tu, Jia-Lin published the artcileRadical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis, SDS of cas: 20880-92-6, the publication is Organic Letters (2020), 22(3), 1222-1226, database is CAplus and MEDLINE.

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive mols. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermol. cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

Organic Letters published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C9H9BO2, SDS of cas: 20880-92-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhang, Pengfei published the artcileA mild acetolysis procedure for the regioselective removal of isopropylidene in di-O-isopropylidene-protected pyranoside systems, Computed Properties of 20880-92-6, the publication is Carbohydrate Research (2017), 7-13, database is CAplus and MEDLINE.

A mild acetolysis method for the regioselective removal of isopropylidene group from di-O-isopropylidene-protected hexopyranosides is reported. O-Isopropylidene-protected intermediates play an important role in carbohydrate chem., as they are often found in com. available furanosyl and pyranosyl materials, and some of them contain more than one O-isopropylidene groups. Methods that permit regioselective removal of O-isopropylidene groups are extremely valuable, as the number of steps in the total synthesis of complex oligosaccharides could be significantly decreased. Here we report that trifluoroacetic acid (TFA)/acetic anhydride (Ac₂O) can be used to regioselectively convert one of the two O-isopropylidene groups to vicinal di-O-acetates in the di-O-isopropylidene-protected galacto- and fructopyranosyl systems, and the reagent is compatible with some common functionalities such as sulfonate esters, bromide, azide etc.

Carbohydrate Research published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C8H5F3O2S, Computed Properties of 20880-92-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts