Tag: 200-300

Excited-State Palladium-Catalyzed Radical Migratory Mizoroki-Heck Reaction Enables C2-Alkenylation of Carbohydrates was written by Yao, Wang;Zhao, Gaoyuan;Wu, Yue;Zhou, Lin;Mukherjee, Upasana;Liu, Peng;Ngai, Ming-Yu. And the article was included in Journal of the American Chemical Society in 2022.Safety of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol This article mentions the following:

Excited-state palladium catalysis has emerged as a promising strategy for developing novel and valuable reactions. Herein, we report the first excited-state Pd-catalyzed 1,2-radical migratory Mizoroki-Heck reaction that enables C2-alkenylation of carbohydrates using readily available 1-bromosugars and alkenes. The reaction tolerates a wide variety of functional groups and complex mol. architectures, including derivatives of natural products and marketed drugs. Preliminary mechanistic studies and DFT calculations suggest the involvement of visible-light-induced photoexcitation of Pd species, 1,2-spin-centered-shift (SCS) process, and Heck-type cross-coupling reaction. The reaction expands the reactivity profile of excited-state Pd catalysis and provides a streamlined protocol for the preparation of a wide variety of C2-alkenylated carbohydrate mimetics to aid the discovery and development of new therapeutics, agrochems., and materials. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Safety of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.Safety of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Dual-Sensitive Nanomicelles Enhancing Systemic Delivery of Therapeutically Active Antibodies Specifically into the Brain was written by Xie, Jinbing;Gonzalez-Carter, Daniel;Tockary, Theofilus A.;Nakamura, Noriko;Xue, Yonger;Nakakido, Makoto;Akiba, Hiroki;Dirisala, Anjaneyulu;Liu, Xueying;Toh, Kazuko;Yang, Tao;Wang, Zengtao;Fukushima, Shigeto;Li, Junjie;Quader, Sabina;Tsumoto, Kouhei;Yokota, Takanori;Anraku, Yasutaka;Kataoka, Kazunori. And the article was included in ACS Nano in 2020.Category: tetrahydrofurans This article mentions the following:

Delivering therapeutic antibodies into the brain across the blood-brain barrier at a therapeutic level is a promising while challenging approach in the treatment of neurol. disorders. Here, we present a polymeric nanomicelle (PM) system capable of delivering therapeutically effective levels of 3D6 antibody fragments (3D6-Fab) into the brain parenchyma for inhibiting Aβ aggregation. PM assembly was achieved by charge-converting 3D6-Fab through pH-sensitive citraconylation to allow complexation with reductive-sensitive cationic polymers. Brain targeting was achieved by functionalizing the PM surface with glucose mols. to allow interaction with recycling glucose transporter (Glut)-1 proteins. Consequently, 41-fold enhanced 3D6-Fab accumulation in the brain was achieved by using the PM system compared to free 3D6-Fab. Furthermore, therapeutic benefits were obtained by successfully inhibiting Aβ_1-42 aggregation in Alzheimer’s disease mice systemically treated with 3D6-Fab-loaded glucosylated PM. Hence, this nanocarrier system represents a promising method for effectively delivering functional antibody agents into the brain and treating neurol. diseases. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Category: tetrahydrofurans).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran and dihydrofuran form the basic structural unit of many naturally occurring scaffolds like gambieric acid A and ciguatoxin, goniocin, and some biologically active molecules. Tetrahydrofuran (THF) is primarily used as a precursor to polymers including for surface coating, adhesives, and printing inks.Category: tetrahydrofurans

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Electrochemical Organoselenium-Catalyzed Intermolecular Hydroazolylation of Alkenes with Low Catalyst Loadings was written by Tan, Zhoumei;Xiang, Fang;Xu, Kun;Zeng, Chengchu. And the article was included in Organic Letters in 2022.Name: (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol This article mentions the following:

The organoselenium-catalyzed amination of alkenes was a promising way to construct functionalized amines. However, the use of chem. oxidants and the unavoidable formation of allylic amine or enamine were the two main limitations of these methodologies. Against this background, herein reported an electro-selenocatalytic regime for the hydroazolylation of alkenes with azoles under external oxidant-free conditions with low catalyst loadings. Moreover, this protocol enabled the generation of amines without vinyl substituents. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Name: (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. Tetrahydrofuran (THF) is primarily used as a precursor to polymers including for surface coating, adhesives, and printing inks.Name: (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Reactivity, Selectivity, and Synthesis of 4-C-Silylated Glycosyl Donors and 4-Deoxy Analogues was written by Jaeger Pedersen, Martin;Pedersen, Christian Marcus. And the article was included in Angewandte Chemie, International Edition in 2021.Reference of 582-52-5 This article mentions the following:

A method for introducing dimethylphenylsilyl at the 4-position in carbohydrates has been developed. Two C-silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3-OH, 4-OH, and 6-OH. Compared with the 4-deoxy variant, it was found that the anomeric selectivity was influenced more by the C-2 substituents orientation than the silyl in the 4-position. In general, the reactivity of these donors was higher than the corresponding 4-deoxy-analog, albeit a competition experiment showed that the introduction of a C-Si increases the relative reactivity by a modest factor of around two. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Reference of 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran and dihydrofuran form the basic structural unit of many naturally occurring scaffolds like gambieric acid A and ciguatoxin, goniocin, and some biologically active molecules. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Reference of 582-52-5

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Cyanomethyl Ether as an Orthogonal Participating Group for Stereoselective Synthesis of 1,2-trans-β-O-Glycosides was written by Molla, Mosidur Rahaman;Das, Pradip;Guleria, Kanika;Subramanian, Ranga;Kumar, Amit;Thakur, Rima. And the article was included in Journal of Organic Chemistry in 2020.Synthetic Route of C12H20O6 This article mentions the following:

Stereoselective formation of glycosidic linkages has been the prime focus for contemporary carbohydrate chem. Herein, we report cyanomethyl (CNMe) ether as an efficient and effective participating orthogonal protecting group for the stereoselective synthesis of 1,2-trans-β-O-glycosides. The participating group facilitated good to high β-selective glycosylation with a broad range of electron-rich and electron-deficient glycosyl acceptors. Detailed exptl. and theor. studies reveal the involvement of CNMe ether in the formation of a six-membered imine-type cyclic intermediate for the observed stereoselectivity. Rapid incorporation and selective removal of the CNMe ether group in the presence of benzyl ether and isopropylidene acetal protection have also been reported here. The nitrile group provided an opportunity for the glyco-diversification through further derivatization. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Synthetic Route of C12H20O6).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Commercial tetrahydrofuran contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although tetrahydrofuran is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.Synthetic Route of C12H20O6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Stereoselective Phenylseleno-glycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides was written by Meng, Shuai;Zhong, Wenhe;Yao, Wang;Li, Zhongjun. And the article was included in Organic Letters in 2020.Product Details of 582-52-5 This article mentions the following:

A phenylseleno-glycosylation reaction of glycal derivatives mediated by di-Ph diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, resp. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Product Details of 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives.Tetrahydrofuran has many industry uses as a solvent including in natural and synthetic resins, high polymers, fat oils, rubber, polymer. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.Product Details of 582-52-5

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Efficient Divergent Synthesis of 2′-O,4′-C-Ethylene-Bridged Nucleic Acid (ENA) Phosphoramidites was written by Abe, Yuzo;Ukai, Kazutoshi;Michida, Makoto. And the article was included in Organic Process Research & Development in 2022.SDS of cas: 582-52-5 This article mentions the following:

2′-O,4′-C-Ethylene-bridged nucleic acid (ENA) phosphoramidites are highly promising modified nucleic acid monomers discovered by Daiichi Sankyo. To increase the productivity of manufacturing, we have developed a highly efficient synthetic method for ENA phosphoramidites. The basic concept of the new synthetic route is “divergent synthesis” for the preparation of four types of monomers such as A, G, C, and T. We applied stereoselective glycosylation reactions without utilizing neighboring group participation to set a common intermediate in the downstream of the route. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5SDS of cas: 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF) is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II). Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.SDS of cas: 582-52-5

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Novel Position-Specific ¹⁸O/¹⁶O Measurement of Carbohydrates. II. The Complete Intramolecular ¹⁸O/¹⁶O Profile of the Glucose Unit in a Starch of C4 Origin was written by Ma, Ran;Zhao, Yu;Liu, Lan;Zhu, Zhenyu;Wang, Bo;Wang, Ying;Yin, Xijie;Su, Jing;Zhou, Youping. And the article was included in Analytical Chemistry (Washington, DC, United States) in 2020.Computed Properties of C12H20O6 This article mentions the following:

Information about plant photosynthetic carbon assimilation, physiol., and biochem. is locked in the ¹⁸O/¹⁶O ratios of the individual positions of higher plants carbohydrates but is under-utilized due to the difficulty of making these determinations We report the extension of the wet chem. approach we used to access the ¹⁸O/¹⁶O ratio of O-3 of glucose with a novel GC/Pyrolysis/IRMS-based method, to determine the ¹⁸O/¹⁶O ratios of O-4, O-5 and O-6. The O atoms (OH groups) at positions 1, 2, 5 and 6 of glucose were protected by acetonation (converting to 1,2;5,6-di-O-isopropylidene-glucofuranose, DAGF). The DAGF was then converted to 6-bromo-6-deoxy-1,2;3,5-di-O-isopropylidene-glucofuranose (6-bromo-DAGF) and Rayleigh-type fractionation. Isotope mass balance was then applied to calculate the ¹⁸O/¹⁶O of O-5 and O-6 as a whole and O-6 resp. Quant. conversion of glucose with phenylhydrazine to phenylglucosazone also allowed for the calculation of ¹⁸O₂ by applying isotope mass balance between the two. A C₄ starch-derived glucose intramol. ¹⁸O profile is now determined: O-3 is relatively enriched (by 12.16mUr), O-4 relatively depleted (by 20.40-31.11mUr) and O-2 marginally enriched (by 2.40mUr) against the mol. average In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Computed Properties of C12H20O6).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF), or oxolane, is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. Tetrahydrofuran (THF) is primarily used as a precursor to polymers including for surface coating, adhesives, and printing inks.Computed Properties of C12H20O6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Chemical synthesis and pharmacological properties of heparin pentasaccharide analogues was written by Zhou, Zhipeng;Zhang, Linlin;Wu, Xin;Luo, Lan;Wu, Jian;Xu, Dan;Wu, Mingyi. And the article was included in European Journal of Medicinal Chemistry in 2022.HPLC of Formula: 582-52-5 This article mentions the following:

The pentasaccharide fondaparinux is a synthetic anticoagulant based on heparin antithrombin-binding sequence. Fondaparinux improves safety and predictable pharmacodynamics compared with heparins; however, it requires a complicate synthesis process which contain more than 50 steps of synthesis. Herein, we designed and synthesized four fondaparinux analogs (compounds 1, 2, 3, 4) using a [2+3] convergent synthetic method, which greatly simplified the synthetic process, improved the product yield, and curtailed the expenditures. These synthesized compounds showed stronger anticoagulant activities by factor Xa inhibition (IC₅₀ 725-1126 nM vs. 1909 nM for fondaparinux) in the AT-dependent manner. After s.c. (s.c.) administration to rats, the compounds displayed long-lasting anti-factor Xa activities and inhibition of thrombin generation ex vivo. Compared with fondaparinux, these compounds were slowly eliminated after s.c. administration to rats, the half-lies (t_1/2) were more than 2-fold of that of fondaparinux. These results suggested the pentasaccharide analogs may exhibit better pharmacokinetic and predictable pharmacodynamic characteristics. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5HPLC of Formula: 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Tetrahydrofuran can also be produced, or synthesised, via catalytic hydrogenation of furan. This process involves converting certain sugars into THF by digesting to furfural. An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.HPLC of Formula: 582-52-5

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Organic-Photoacid-Catalyzed Glycosylation was written by Li, Juncheng;Zhao, Gaoyuan;Wang, Ting. And the article was included in Synlett in 2020.Electric Literature of C12H20O6 This article mentions the following:

Photoacids are mols. that become more acidic upon absorption of light. They are widely utilized in a variety of fields, such as organic synthesis, mol. switching agents, and photodynamic therapy. Currently, the activity of most photo-acids is induced by UV light, which limits their applications by the synthetic community. In this Synpacts article, we highlight our recent development of visible-light-induced photo-acids and their application in glycosylation reactions. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Electric Literature of C12H20O6).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. Tetrahydrofuran (THF) is primarily used as a precursor to polymers including for surface coating, adhesives, and printing inks.Electric Literature of C12H20O6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem