Category: 144490-03-9

Forsman, Jonas J.;Waerna, Johan;Murzin, Dmitry Yu.;Leino, Reko published 《Reaction Kinetics and Mechanism of Sulfuric Acid-Catalyzed Acetolysis of Acylated Methyl L-Ribofuranosides》. The research results were published in《European Journal of Organic Chemistry》 in 2009.Application of 144490-03-9 The article conveys some information:

The mechanism of the sulfuric acid-catalyzed acetolysis of Me 2,3,5-tri-O-acetyl- and Me 2,3,5-tri-O-benzoyl-L-ribofuranosides and the accompanying anomerization of both the starting material and the 1,2,3,5-tetra-O-acetyl- and 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranoses formed was investigated. The progress of the reactions was followed by ¹H NMR spectroscopy and the rate constants for the reactions were determined for a proposed kinetic model. The role of H⁺ and Ac⁺ as the catalytically active species was clarified, proving that the anomerization of the acylated Me furanosides is activated by protonation, while, on the contrary, the anomerization of the 1-O-acetyl ribofuranoses is activated by the acetyl cation. The anomerization of the acylated Me furanosides was verified to be activated on the ring oxygen leading to endocyclic CO-bond rupture while the 1-O-acetyl ribofuranoses are activated on the acetyloxy group on C(1) leading to exocyclic cleavage. (© Wiley-VCH Verlag GmbH and Co. KGaA, 69451 Weinheim, Germany, 2009). 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 Application of 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

Shi, Z.-D.;Yang, B.-H.;Wu, Y.-L. published 《A stereospecific synthesis of L-ribose and L-ribosides from D-galactose》. The research results were published in《Tetrahedron Letters》 in 2001.Computed Properties of C13H18O9 The article conveys some information:

An inexpensive D-galactose was converted into L-ribose and its derivatives via mild reaction conditions. The L-ribosyl donor was submitted to a glycosidation according to Vorbruggen’s conditions to give L-riboside nucleosides, e.g. L-adenosine, in high yields. 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 Computed Properties of C13H18O9) 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

Chen, Yao;Ran, Xu;Zhang, Jiancun;Fu, Lei published 《Preparation of L-nucleosides with benzyl as protecting group》 in 2008. The article was appeared in 《Huaxue Yanjiu Yu Yingyong》. They have made some progress in their research.Formula: C13H18O9 The article mentions the following:

A method for the synthesis of the title compounds is reported here. 3-Benzyl-L-uridine [i.e., 1-(β-L-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione] and 6-benzyl-L-adenosine [i.e., N-(phenylmethyl)-9-β-L-ribofuranosyl-9H-purin-6-amine] were synthesized as intermediates for L-nucleoside compounds with potential antiviral activity (no data). The synthetic procedures used β-L-Ribofuranose tetraacetate as starting material. The structures were confirmed by NMR, elemental anal. and optical rotation. 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 Formula: C13H18O9) 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

Application In Synthesis of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateIn 2016, Li, Guo-Xing;Morales-Rivera, Christian A.;Wang, Yaxin;Gao, Fang;He, Gang;Liu, Peng;Chen, Gong published 《Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine》. 《Chemical Science》published the findings. The article contains the following contents:

A photoredox-mediated Minisci C-H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)₃]Cl₂ as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, and offers a broadly applicable method for late-stage functionalization of complex substrates. Mechanistic experiments and computational studies suggest that an intramolecularly stabilized ortho-iodobenzoyloxy radical intermediate might play a key role in this reaction system. 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 Application In Synthesis 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

COA of Formula: C13H18O9In 2011, Pan, Mei-Ying;Hang, Wen;Zhao, Xiao-Jun;Zhao, Hang;Deng, Peng-Chi;Xing, Zhi-Hua;Qing, Yong;He, Yang published 《Janus-type AT nucleosides: synthesis, solid and solution state structures》. 《Organic & Biomolecular Chemistry》published the findings. The article contains the following contents:

Novel Janus-type nucleoside analogs (1a-d) were synthesized. Their pyrimido[4,5-d]pyrimidine base moiety has one face with a bidentate Watson-Crick donor-acceptor (DA) H-bond array of adenine and the other face with an acceptor-donor (AD) H-bond array of thymine. These nucleosides may self-associate through the self-complementary base pair. Indeed, in the solid state, compound 6d displayed a honeycomb-like supramol. structure with tetrameric membered cavities formed through the combination of reverse Watson-Crick base pairs and aromatic stacking, in which the solvent mols. were accommodated. The result of temperature-dependent CD studies showed that the free nucleosides can form higher order chiral structures in aqueous solution 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 COA of Formula: C13H18O9) 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

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

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

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

Synthetic Route of C13H18O9《Thio-Linked UDP-Peptide Conjugates as O-GlcNAc Transferase Inhibitors》 was published in 2018. The authors were Rafie, Karim;Gorelik, Andrii;Trapannone, Riccardo;Borodkin, Vladimir S.;van Aalten, Daan M. F., and the article was included in《Bioconjugate Chemistry》. The author mentioned the following in the article:

O-GlcNAc transferase (OGT) is an essential glycosyltransferase that installs the O-GlcNAc post-translational modification on the nucleocytoplasmic proteome. We report the development of S-linked UDP-peptide conjugates as potent bisubstrate OGT inhibitors. These compounds were assembled in a modular fashion by photoinitiated thiol-ene conjugation of allyl-UDP and optimal acceptor peptides in which the acceptor serine was replaced with cysteine. The conjugate VTPVC(S-propyl-UDP)TA (K_i = 1.3 μM) inhibits the OGT activity in HeLa cell lysates. Linear fusions of this conjugate with cell penetrating peptides were explored as prototypes of cell-penetrant OGT inhibitors. A crystal structure of human OGT with the inhibitor revealed mimicry of the interactions seen in the pseudo-Michaelis complex. Furthermore, a fluorophore-tagged derivative of the inhibitor works as a high affinity probe in a fluorescence polarimetry hOGT assay. 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 Synthetic Route of C13H18O9) 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