Heterocyclic Building Blocks-Tetrahydrofuran

Safety of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateIn 2017, Amdouni, Hella;Robert, Guillaume;Driowya, Mohsine;Furstoss, Nathan;Metier, Camille;Dubois, Alix;Dufies, Maeva;Zerhouni, Marwa;Orange, Francois;Lacas-Gervais, Sandra;Bougrin, Khalid;Martin, Anthony R.;Auberger, Patrick;Benhida, Rachid published 《In Vitro and in Vivo Evaluation of Fully Substituted (5-(3-Ethoxy-3-oxopropynyl)-4-(ethoxycarbonyl)-1,2,3-triazolyl-glycosides as Original Nucleoside Analogues to Circumvent Resistance in Myeloid Malignancies》. 《Journal of Medicinal Chemistry》published the findings. The article contains the following contents:

A series of nucleoside analogs, e.g. I, bearing a 1,4,5-tri-substituted-1,2,3-triazole aglycon was synthesized using a straightforward click/electrophilic addition or click/oxidative coupling tandem procedures. SAR anal., using cell culture assays, led to the discovery of a series of compounds belonging to the 5-alkynyl-1,2,3-triazole family that exhibits potent antileukemic effects on several hematol. malignancies including chronic myeloid leukemia (CML) and myelodysplastic syndromes (MDS) either sensitive or resistant to their resp. therapy. Compound I also proved efficient in vivo on mice xenografted with SKM1-R MDS cell line. Addnl., some insights in its mode of action revealed that this compound can induce cell death by caspase and autophagy induction. To complete the study, the researchers used (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) .

(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 Safety of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

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

Bercot, Eric A.;Rovis, Tomislav published 《Highly Efficient Nickel-Catalyzed Cross-Coupling of Succinic and Glutaric Anhydrides with Organozinc Reagents》 in 2005. The article was appeared in 《Journal of the American Chemical Society》. They have made some progress in their research.Application In Synthesis of (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione The article mentions the following:

A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate scope with respect to electrophilic and nucleophilic coupling partners has been examined and found to be remarkably broad, allowing for rapid introduction of mol. complexity through the use of functionalized coupling partners. Regioselective alkylation of an unsym. succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event. To complete the study, the researchers used (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Application In Synthesis of (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Guo, Xiurong;Xin, Guang;He, Shiliang;Wang, Yanyan;Huang, Baozhan;Zhao, Hang;Xing, Zhihua;Chen, Qingming;Huang, Wen;He, Yang published 《Novel organic gelators based on pentose derivatized diosgenyl saponins》 in 2013. The article was appeared in 《Organic & Biomolecular Chemistry》. They have made some progress in their research.HPLC of Formula: 144490-03-9 The article mentions the following:

Much attention has been paid to diosgenin saponins because of their various bioactivities, whereas their gelation ability has never been reported. We synthesized some new saponins with pentose directly connected to diosgenin in a shorter procedure, which neither removed the acetyl group of the anomeric hydroxyl group selectively nor activated it and led to a higher yield, compared with the common synthesis of other diosgenyl saponins. We found these compounds are gelators of various organic solvents and their gel formation was studied with FTIR and SEM. This serendipitous discovery enriches the diversity of steroidal small mol. gelators. Meanwhile, single crystal X-ray anal. gave addnl. information about their intermol. interactions in the solid state. And (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) was used in the research process.

(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 HPLC of Formula: 144490-03-9) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

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

Polonski, Tadeusz;Milewska, Maria J.;Gdaniec, Maria;Gilski, Miroslaw published 《Molecular geometry and circular dichroism spectra of bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydrides and imides》 in 1993. The article was appeared in 《Journal of Organic Chemistry》. They have made some progress in their research.Category: tetrahydrofurans The article mentions the following:

Several tricyclic anhydrides and imides derived from optically active bicyclo[2.2.1]heptane-2,3-dicarboxylic acids were synthesized, and their CD spectra are reported. On the basis of MNDO calculations it was estimated that despite rigidity of the norbornane system, the five-membered rings of succinic anhydride and imide moieties are slightly twisted. The chromophores are flexible and can be more or less skewed depending on solvent polarity. The chromophore nonplanarity significantly influences magnitude and sign of the first Cotton effect associated with the lowest energy n-π^* electronic transition. The sign of the second n-π^* Cotton effect is governed by vicinal effect of substituents. The crystal structures of three N-(S)-1-phenylethylimides were solved to estimate the configuration of C-2 of the imide moieties.(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) were involved in the experimental procedure.

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Category: tetrahydrofurans It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Recommanded Product: (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione《Study of Chemical Shift Variations in Tricyclic Urazoles with a Norbornane Skeleton》 was published in 2006. The authors were Bentz, Timothy;Ryzhkov, Lev, and the article was included in《Spectroscopy Letters》. The author mentioned the following in the article:

Mols. related to norbornane commonly serve as useful models for stereochem. and conformational anal., as well as for elucidation of steric and electronic substituent effects. Chem. shifts of their bridge protons are well tabulated and follow clear, easily predictable patterns. For example, the exo protons on a two-carbon bridge of these mols. are typically deshielded relative to the endo protons. Previously, some exceptions to this rule were noted and satisfactorily explained. In tricyclic urazoles, common precursors to cyclic diazenes, the order of chem. shifts of exo and endo bridge protons is reversed. The authors use aromatic solvent induced shifts (ASIS) and homodecoupling experiments to assign ¹H-NMR signals in these urazoles and bridge proton signals in model mols., and the authors discuss anal. of factors that influence chem. shifts in this polycyclic system. The experimental procedure involved many compounds, such as (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Recommanded Product: (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Ishizumi, Kikuo;Kojima, Atsuyuki;Antoku, Fujio published 《Synthesis and anxiolytic activity of N-substituted cyclic imides (1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide (tandospirone) and related compounds》 in 1991. The article was appeared in 《Chemical & Pharmaceutical Bulletin》. They have made some progress in their research.Application of 14166-28-0 The article mentions the following:

A series of cyclic imides bearing ω-(4-aryl and 4-heteroaryl-1-piperazinyl)alkyl moieties, e.g., I, was synthesized and tested in vivo for anxiolytic activity. The in vitro binding affinities of these compounds were also examined for 5-HT_1A receptor sites. Structure-activity relationships within the series are discussed. Tandospirone (I) was equipotent with buspirone in its anxiolytic activity and more anxio-selective than buspirone and diazepam. I is currently undergoing clin. evaluation as a selective anxiolytic agent.(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) were involved in the experimental procedure.

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Application of 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Zhou, Zheng Hong;Chen, Ru Yu published 《Synthesis of 1,2-cyclic monoacyl-rac-glycerothiophosphates of cantharidin analogues》 in 2000. The article was appeared in 《Phosphorus, Sulfur and Silicon and the Related Elements》. They have made some progress in their research.HPLC of Formula: 14166-28-0 The article mentions the following:

1,2-Cyclic monoacyl-rac-glycerothiophosphates of cantharidin and its analogs, e.g., I (R = H, X = O, CH₂) were synthesized in a 1-pot procedure in overall yields of 44-55.5% by P(NEt₂)₃, activated by a catalytic amount of iodine, as phosphorylating reagent, acting on N-hydroxyethyl exo-(7-oxa)bicyclo[2.2.1]heptene-2,3-dicarboximide followed by a cyclocondensation with monostearin. Their structures were confirmed by ¹H NMR, ³¹P NMR, IR and elemental anal. The experimental procedure involved many compounds, such as (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.HPLC of Formula: 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Li, Guo-Xing;Morales-Rivera, Cristian A.;Wang, Yaxin;Gao, Fang;He, Gang;Liu, Peng;Chen, Gong published 《Correction: Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine [Erratum to document cited in CA165:353819]》. The research results were published in《Chemical Science》 in 2016.Category: tetrahydrofurans The article conveys some information:

In the original publication, author Cristian A. Morales-Rivera′s name is spelled incorrectly; the correction is made here. And (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) was used in the research process.

(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 Category: tetrahydrofurans) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

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

To, Kenneth K. W.;Wang, Xinning;Yu, Chun Wing;Ho, Yee-Ping;Au-Yeung, Steve C. F. published 《Protein phosphatase 2A inhibition and circumvention of cisplatin cross-resistance by novel TCM-platinum anticancer agents containing demethylcantharidin》. The research results were published in《Bioorganic & Medicinal Chemistry》 in 2004.COA of Formula: C9H10O3 The article conveys some information:

Novel TCM-platinum compounds [Pt(C₈H₈O₅)(NH₂R)₂], derived from integrating demethylcantharidin, a modified component from a traditional Chinese medicine (TCM) with a platinum moiety, possess anticancer and protein phosphatase 2A (PP2A) inhibition properties. The compounds are able to circumvent cisplatin resistance by apparently targeting the DNA repair mechanism. Novel isosteric analogs [Pt(C₉H₁₀O₄)(NH₂R)₂], devoid of PP2A-inhibitory activity, were found to suffer from an enhanced DNA repair and were cross-resistant to cisplatin. The results advocate a well-defined structure-activity requirement associating the PP2A-inhibiting demethylcantharidin with the circumvention of cisplatin cross-resistance demonstrated by TCM-Pt compounds(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) were involved in the experimental procedure.

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

COA of Formula: C9H10O3《Cantharidin analogs and their attractancy for ceratopogonid flies (Diptera: Ceratopogonidae)》 was published in 1992. The authors were Frenzel, M.;Dettner, K.;Wirth, D.;Waibel, J.;Boland, W., and the article was included in《Experientia》. The author mentioned the following in the article:

Several ceratopogonid flies are attracted to cantharidin and ingest it from both cantharidin-baits and from meloid beetles, one of the few known natural sources for cantharidin. Because meloids are absent in northern Bavaria, and certain canthariphilous flies of the genus Atrichopogon are temporarily associated with certain plants (Apiaceae, Aristolochiaceae), it was suggested that canthariphilous ceratopogonids might be generally attracted by chem. similar plant-derived compounds At first the seasonal fluctuating attractancy, sex ratio, and behavior of A. oedemerarum was studied at cantharidin baits. Synthetic cantharidin analogs exhibited an attractancy for A. oedemerarum if the exo,exo-7-oxabicyclo[2.2.1]heptane skeleton of cantharidin was associated with a 2,3-dicarboxylic anhydride or a 2,3-γ-lactone. According to the structure-activity studies, the analogs seem to fit best into the active site of the receptor if the carbonyl function of the γ-lactone is in the exo- and 2-position. This is the first report indicating that mols. other than cantharidin are attractive for canthariphilous insects. To complete the study, the researchers used (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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