Tag: 200-300

Attempted synthesis of central furopyran core of Diocollettines A via a Gold-Catalyzed cascade 1,6-Diyne cycloisomerization process was written by Mullapudi, Venkannababu;Ramana, Chepuri V.. And the article was included in Tetrahedron Letters in 2020.Product Details of 582-52-5 This article mentions the following:

Herein, we describe an Au-catalyzed cascade diyne cycloisomerization process that was projected to construct the central furopyran bicyclic core of Diocollettines A, I. Our intended strategy for the annulation of the third THF ring is based on epoxidation and subsequent intramol. acetalization. However, the initial alkynol cyclization occurred in an undesired 5-exo-dig mode, ultimately leading to an undesired furopyran. 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. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Product Details of 582-52-5

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

NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides was written by Liu, Rongkun;Hua, Qingting;Lou, Qixin;Wang, Jiazhe;Li, Xiaona;Ma, Zhi;Yang, You. And the article was included in Journal of Organic Chemistry in 2021.Computed Properties of C12H20O6 This article mentions the following:

Glycosidation plays a pivotal role in the synthesis of O-glycosides and nucleosides that mediate a diverse range of biol. processes. However, efficient glycosidation approach for the synthesis of both O-glycosides and nucleosides remains challenging in terms of glycosidation yields, mild reaction conditions, readily available glycosyl donors, and cheap promoters. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf)-promoted glycosidation approach with glycosyl ortho-hexynylbenzoates as donors for the highly efficient synthesis of O-glycosides and nucleosides. The glycosidation approach highlights the merits of mild reaction conditions, cheap promoters, extremely wide substrate scope, and good to excellent yields. Notably, the glycosidation approach performs very well in the construction of a series of challenging O- and N-glycosidic linkages. The glycosidation approach is then applied to the efficient synthesis of oligosaccharides via the one-pot strategy and the stepwise strategy. On the basis of the isolation and characterization of the departure species derived from the leaving group, a plausible mechanism of NIS/TMSOTf-promoted glycosidation of glycosyl ortho-hexynylbenzoates is proposed. 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. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. THF can also be synthesized by catalytic hydrogenation of furan. This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced. THF is thus derivable from renewable resources.Computed Properties of C12H20O6

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

Development of a Flexible and Robust Synthesis of Tetrahydrofuro[3,4-b]furan Nucleoside Analogs as PRMT5 inhibitors was written by Candito, David A.;Ye, Yingchun;Quiroz, Ryan V.;Reutershan, Michael H.;Witter, David;Gadamsetty, Surendra B.;Li, Hongming;Sauri, Josep;Schneider, Sebastian E.;Lam, Yu-hong;Palte, Rachel L.. And the article was included in Journal of Organic Chemistry in 2021.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:

In the context of a PRMT5 inhibitor program, we describe our efforts to develop a flexible and robust strategy to access tetrahydrofuro[3,4-b]furan nucleoside analogs, e.g. I. Ultimately, it was found that a Wolfe type carboetherification from an alkenol derived from D-glucofuranose diacetonide was capable of furnishing the B-ring and installing the desired heteroaryl group in a single step. Compound I was profiled in biochem. and cellular assays and was demonstrated to be a potent and cellularly active PRMT5 inhibitor, with a PRMT5-MEP50 biochem. IC₅₀ of 0.8 nM, a MCF-7 target engagement EC₅₀ of 3 nM, and a Z138 cell proliferation EC₅₀ of 15 nM. This work sets the stage for the development of new inhibitors of PRMT5 and novel nucleoside chem. matter for alternate drug discovery programs. 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. Tetrahydrofuran (THF) is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II). Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.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

Structural Basis for Blocking Sugar Uptake into the Malaria Parasite Plasmodium falciparum was written by Jiang, Xin;Yuan, Yafei;Huang, Jian;Zhang, Shuo;Luo, Shuchen;Wang, Nan;Pu, Debing;Zhao, Na;Tang, Qingxuan;Hirata, Kunio;Yang, Xikang;Jiao, Yaqing;Sakata-Kato, Tomoyo;Wu, Jia-Wei;Yan, Chuangye;Kato, Nobutaka;Yin, Hang;Yan, Nieng. And the article was included in Cell (Cambridge, MA, United States) in 2020.Related Products of 582-52-5 This article mentions the following:

Plasmodium species, the causative agent of malaria, rely on glucose for energy supply during blood stage. Inhibition of glucose uptake thus represents a potential strategy for the development of antimalarial drugs. Here, we present the crystal structures of PfHT1, the sole hexose transporter in the genome of Plasmodium species, at resolutions of 2.6 Å in complex with D-glucose and 3.7 Å with a moderately selective inhibitor, C3361. Although both structures exhibit occluded conformations, binding of C3361 induces marked rearrangements that result in an addnl. pocket. This inhibitor-binding-induced pocket presents an opportunity for the rational design of PfHT1-specific inhibitors (hexose transporter HT1 inhibitors). Among our designed C3361 derivatives, several exhibited improved inhibition of PfHT1 and cellular potency against P. falciparum, with excellent selectivity to human GLUT1. These findings serve as a proof of concept for the development of the next-generation antimalarial chemotherapeutics by simultaneously targeting the orthosteric and allosteric sites of PfHT1. 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: 582-52-5Related Products 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. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Related Products of 582-52-5

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

Radiosynthesis of ¹⁸F-labeled D-allose was written by Yamamoto, Hiroyuki;Wada, Kenji;Toyohara, Jun;Tago, Tetsuro;Ibaraki, Masanobu;Kinoshita, Toshibumi;Yamamoto, Yuka;Nishiyama, Yoshihiro;Kudomi, Nobuyuki. And the article was included in Carbohydrate Research in 2019.Synthetic Route of C12H20O6 This article mentions the following:

Rare sugars are defined as monosaccharides that exist in nature but are only present in limited quantities. D-Allose is a rare sugar that has been reported to have some unique physiol. effects. The present study describes suitable synthetic procedures for novel rare sugars of D-allose that are ¹⁸F-labeled at the C-3 and C-6 positions and the preparation of the appropriate labeling precursors. The goal is to facilitate in vivo, noninvasive positron emission tomog. (PET) investigation of the behavior of rare sugar analogs of D-allose in organs. We found five precursors that were practical for labeling, three for 3-deoxy-3-[¹⁸F]fluoro-D-allose ([¹⁸F]3FDA) and two for 6-deoxy-6-[¹⁸F]fluoro-D-allose ([¹⁸F]6FDA). With manual operation synthesis, the highest radiochem. conversion rates were 75% for [¹⁸F]3FDA with a precursor of 1,2,4,6-tetra-O-acetyl-3-O-trifluoromethanesulfonyl-β-D-glucopyranose and 69% for [¹⁸F]6FDA with a precursor of 1,2,3,4-tetra-O-acetyl-6-O-trifluoromethanesulfonyl-β-D-allopyranose. Furthermore, the practical yields of [¹⁸F]3FDA and [¹⁸F]6FDA using an automated synthesizer were also investigated. Radiochem. yields of 67% and 49% were obtained for [¹⁸F]3FDA and [¹⁸F]6FDA, resp., in an automated synthesizer. As basic assessment of stability for use in PET scanning, high performance liquid chromatog. anal. showed no decomposition of [¹⁸F]3FDA and [¹⁸F]6FDA after up to 6 h in rabbit blood plasma. 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 water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Synthetic Route of C12H20O6

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

Construction of key building blocks towards the synthesis of cortistatins was written by Indu, Satrajit;Telore, Rahul D.;Kaliappan, Krishna P.. And the article was included in Organic & Biomolecular Chemistry in 2020.Application In Synthesis 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:

This work reports the construction of key building blocks towards the synthesis of cortistatins, a family of steroidal alkaloids. Cortistatin A (I), being a primary target due to its superior biol. properties over other congeners, has been prepared by two different synthetic routes. Synthesis of the precursor to the heavily substituted A-ring starting from D-glucose and construction of the DE-ring junction employing a Hajos-Parrish ketone as a chiral pool have been demonstrated. Efforts are underway to assemble these key fragments and build towards the total synthesis of cortistatin A. 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: 582-52-5Application In Synthesis 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. 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.Application In Synthesis 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

Base Mediated Diazirination via Iodine(III) Reagents was written by Ansari, Monish Arbaz;Kumar, Ganesh;Singh, Maya Shankar. 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:

An efficient method for the construction of highly functionalized diazirines from the carbohydrazide and diazo-substituted hypervalent iodine reagents was described. Unambiguous transformation was designed with user applicable and easy practicable conditions. Remarkably, D-glucose, menthol, aspirin, proline, and lithocholic acid were efficiently diazirinated. Furthermore, the method was mild, robust, and highly selective, which successfully converted a variety of aryl, alkyl, benzyl, and heterocyclic hydrazides into the corresponding diazirine derivatives 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. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. 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

Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides was written by Siyabalapitiya Arachchige, Sameera;Crich, David. And the article was included in Journal of Organic Chemistry in 2022.HPLC of Formula: 582-52-5 This article mentions the following:

We describe the synthesis and side chain conformational anal. of a series of four 6-deoxy-2,3,5-tri-O-benzyl hexofuranosyl donors with the D-gluco, L-ido, D-altro, and L-galacto configurations. The conformation of the exocyclic bond of these compounds depends on the relative configuration of the point of attachment of the side chain to the ring and of the two flanking centers and can be predicted on that basis analogously to the heptopyranose analogs. Variable-temperature NMR (VT NMR) spectroscopy of the activated donors reveals complex, configuration-dependent mixtures of intermediates that we interpret in terms of fused and bridged oxonium ions arising from participation by the various benzyl ethers. The increased importance of ether participation in the furanoside series compared to the pyranosides is discussed in terms of the reduced stabilization afforded to furanosyl oxocarbenium ions by covalent triflate formation. The stereoselectivities of the four donors are discussed on the basis of the benzyl ether participation model. 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. Tetrahydrofuran (THF) is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II). 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.HPLC of Formula: 582-52-5

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

Red Algal Molecules – Synthesis of Methyl Neo-β-carrabioside and Its S-Linked Variant via Two Synthetic Routes: A Late Stage Ring Closure and Using a 3,6-Anhydro-D-galactosyl Donor was written by Wallace, Michael D.;Ficko-Blean, Elizabeth;Stubbs, Keith A.. And the article was included in Journal of Organic Chemistry in 2020.COA of Formula: C12H20O6 This article mentions the following:

Me neo-β-carrabioside has been synthesized for the first time, employing either a late stage ring closure to install the required 3,6-anhydro-bridge or a suitable 3,6-anhydro-galactosyl donor to form the unfavored 1,2-cis-equatorial α-linkage. Using the late stage ring closure approach, an S-linked analog of Me neo-β-carrabioside was also realized. These compounds have applications in the identification and characterization of marine bacterial exo-α-3,6-anhydro-D-galactosidases that have specific activity on red algal neo-carrageenan oligosaccharides, such as those found in both family 127 and 129 of the glycoside hydrolases. In addition a biochem. assay using the synthesized Me neo-β-carrabioside and the marine bacterial exo-α-3,6-anhydro-D-galactosidase ZgGH129 demonstrates that the min. substrate unit for the enzyme is neo-β-carrabiose. 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: 582-52-5COA of Formula: 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. 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.COA of Formula: C12H20O6

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

Stereoselective Total Synthesis of 4-(S)-Hydroxy-5-(R)-octyldihydrofuran-2-one: Harvestmen Lactone was written by Desireddi, Janardana Reddi;Rao, Mora Mallikarjuna;Murahari, Kiran Kumar;Nimmareddy, Rajashekar Reddy;Mothe, Thirupathi;Lingala, Arun Kumar;Maiti, Bhimcharan;Manchal, Ravinder. And the article was included in ChemistrySelect in 2022.HPLC of Formula: 582-52-5 This article mentions the following:

A facile and stereoselective synthesis of Harvestmen lactone, 4-(S)-hydroxy-5-(R)-octyldihydrofuran-2-one, was accomplished in a linear synthetic approach over 14 steps with an overall yield of 10.1%. This total synthesis was carried out using a chiral pool approach from com. available D-glucose. The key reactions employed in this synthetic approach were Wittig reaction, Barton-McCombie deoxygenation and TEMPO-mediated radical oxidation 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. 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. 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.HPLC of Formula: 582-52-5

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