Category: 144490-03-9

Chan, Joseph H.;Chamberlain, Stanley D.;Biron, Karen K.;Davis, Michelle G.;Harvey, Robert J.;Selleseth, Dean W.;Dornsife, Ronna E.;Dark, Ernest H.;Frick, Lloyd W.;Townsend, Leroy B.;Drach, John C.;Koszalka, George W. published 《Synthesis and evaluation of a series of 2′-deoxy analogues of the antiviral agent 5,6-dichloro-2-isopropylamino-1-(β-L-ribofuranosyl)-1H-benzimidazole (1263W94)》. The research results were published in《Nucleosides, Nucleotides & Nucleic Acids》 in 2000.Reference of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate The article conveys some information:

A series of 2′-deoxy analogs of the antiviral agent 5,6-dichloro-2-isopropylamino-1-(β-L-ribofuranosyl)-1H-benzimidazole (1263W94) were synthesized and evaluated for activity against human cytomegalovirus (HCMV) and for cytotoxicity. The 2-substituents in the benzimidazole moiety correspond to those that were used in the 1263W94 series. In general, as was found in the 1263W94 series, cyclic and branched alkylamino groups were needed for potent activity against HCMV. Three analogs were as potent as 1263W94. Further evaluation of two analogs suggested that these 2′-deoxy analogs may act via a novel mechanism of action similar to that of 1263W94. These 2′-deoxy analogs generally lacked cytotoxicity in vitro. Pharmacokinetic parameters in mice and protein binding properties of one of the analogs (I) were quite similar to 1263W94. However, the oral bioavailability of I was only half of that observed for 1263W94. The experimental procedure involved many compounds, such as (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 Reference 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

Electric Literature of C13H18O9《β-L-Thymidine 5′-triphosphate analogs as DNA polymerase substrates》 was published in 1992. The authors were Van Draanen, Nanine A.;Tucker, S. Craig;Boyd, F. Leslie;Trotter, B. Wesley;Reardon, John E., and the article was included in《Journal of Biological Chemistry》. The author mentioned the following in the article:

β-L-3′-Deoxythymidine 5′-triphosphate (L-ddTTP) and β-L-3′-deoxy-2′,3′-didehydrothymidine 5′-triphosphate (L-d4TTP) were substrates for human immunodeficiency virus (HIV) reverse transcriptase, Escherichia coli DNA polymerase I (Klenow), and Sequenase (modified T7 DNA polymerase). The β-D– and β-L-enantiomers of 5-methyluridine 5′-triphosphate (rTTP) were inhibitors but not substrates of reverse transcriptase. The steady-state K_m values for L-ddTTP and L-d4TTP, with all three enzymes, were 12-70-fold larger than the K_m values for the corresponding D-enantiomers. The K_m value of reverse transcriptase for L-ddTTP was 50-fold larger than that for D-ddTTP because the K_d for L-ddTTP was 5-fold larger than that for D-ddTTP, and the first-order rate constant for incorporation of L-ddTMP into the template-primer was 10% that of the D-enantiomer. The D– and L-enantiomers had k_cat values with reverse transcriptase and Sequenase that were similar to k_cat for the natural substrate, thymidine 5′-triphosphate (dTTP). Thus, the rate determining step appeared to be dissociation of the enzyme-chain-terminated template-primer complex. In contrast, k_cat values for the L-enantiomers with Klenow were only 0.1% that of dTTP, and the k_cat values for the D-enantiomers were 15% the k_cat for dTTP. The reduced k_cat values were due to a change in rate-determining step from dissociation of the Klenow-chain-terminated template-primer complex to an earlier step in the reaction mechanism, presumably catalysis. Thus, these DNA polymerases did not stereospecifically recognize D-nucleoside 5′-triphosphate analogs as substrates. The virucidal activity of some nucleoside analogs against HIV is discussed on the basis of the above results. The experimental procedure involved many compounds, such as (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 Electric Literature 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

Application In Synthesis of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateIn 2005, Herbal, Karim;Kitteringham, John;Voyle, Martyn;Whitehead, Andrew J. published 《Synthesis of the enantiomer of nelarabine》. 《Tetrahedron Letters》published the findings. The article contains the following contents:

A synthesis of the enantiomer of nelarabine is described. Subtle changes in the protecting group strategy allow for an efficient inversion of the C-2′ stereocentre. The experimental procedure involved many compounds, such as (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 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

Safety of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateIn 2020, Wu, Ming-hao;Ai, Su;Chen, Qing;Chen, Xiang-yan;Li, Hong-jin;Li, Yu-lei;Zhao, Xia published 《Effects of Glycosylation and D-Amino Acid Substitution on the Antitumor and Antibacterial Activities of Bee Venom Peptide HYL》. 《Bioconjugate Chemistry》published the findings. The article contains the following contents:

Glycosylation is a promising strategy for modulating the physicochem. properties of peptides. However, the influence of glycosylation on the biol. activities of peptides remains unknown. Here, we chose the bee venom peptide HYL as a model peptide and 12 different monosaccharides as model sugars to study the effects of glycosylation site, number, and monosaccharide structure on the biochem. properties, activities, and cellular selectivities of HYL derivatives Some analogs of HYL showed improvement not only in cell selectivity and proteolytic stability but also in antitumor and antimicrobial activity. Moreover, we found that the helicity of glycopeptides can affect its antitumor activity and proteolytic stability, and the α-linked D-monosaccharides can effectively improve the antitumor activity of HYL. Therefore, it is possible to design peptides with improved properties by varying the number, structure, and position of monosaccharides. What’s more, the glycopeptides HYL-31 and HYL-33 show a promising prospect for antitumor and antimicrobial drugs development, resp. In addition, we found that the D-lysine substitution strategy can significantly improve the proteolytic stability of HYL. Our new approach provides a reference or guidance for the research of novel antitumor and antimicrobial peptide drugs. 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

Levinson, Adam M.;McGee, John H.;Roberts, Andrew G.;Creech, Gardner S.;Wang, Ting;Peterson, Michael T.;Hendrickson, Ronald C.;Verdine, Gregory L.;Danishefsky, Samuel J. published 《Total Chemical Synthesis and Folding of All-L and All-D Variants of Oncogenic KRas(G12V)》. The research results were published in《Journal of the American Chemical Society》 in 2017.Recommanded Product: 144490-03-9 The article conveys some information:

The Ras proteins are essential GTPases involved in the regulation of cell proliferation and survival. Mutated oncogenic forms of Ras alter effector binding and innate GTPase activity, leading to deregulation of downstream signal transduction. Mutated forms of Ras are involved in approx. 30% of human cancers. Despite decades of effort to develop direct Ras inhibitors, Ras has long been considered ‘undruggable’ due to its high affinity for GTP and its lack of hydrophobic binding pockets. Herein, we report a total chem. synthesis of all-L and all-D-amino acid biotinylated variants of oncogenic mutant KRas(G12V). The protein is synthesized using Fmoc-based (Fmoc = 9-fluorenylmethoxycarbonyl) solid-phase peptide synthesis and assembled using combined native chem. ligation and isonitrile-mediated activation strategies. We demonstrate that both KRas(G12V) enantiomers can successfully fold and bind nucleotide substrates and binding partners with observable enantiodiscrimination. By demonstrating the functional competency of a mirror-image form of KRas bound to its corresponding enantiomeric nucleotide triphosphate, this study sets the stage for further bio-chem. studies with this material. In particular, this protein will enable mirror-image yeast surface display experiments to identify all-D peptide ligands for oncogenic KRas, providing a useful tool in the search for new therapeutics against this challenging disease target. 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 Recommanded Product: 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

Hocek, Michal;Silhar, Peter;Shih, I-hung;Mabery, Eric;Mackman, Richard published 《Cytostatic and antiviral 6-arylpurine ribonucleosides. Part 7: Synthesis and evaluation of 6-substituted purine L-ribonucleosides》 in 2006. The article was appeared in 《Bioorganic & Medicinal Chemistry Letters》. They have made some progress in their research.HPLC of Formula: 144490-03-9 The article mentions the following:

A series of purine L-ribonucleosides bearing diverse C-substituents (alkyl, aryl, hetaryl or hydroxymethyl) in the position 6 were prepared by Pd-catalyzed cross-coupling reactions of 6-chloro-9-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)purine with the corresponding organometallics followed by deprotection. Unlike their L-ribonucleoside enantiomers that possess strong cytostatic and anti-HCV activity, the L-ribonucleosides were inactive except for 6-benzylpurine nucleoside showing moderate anti-HCV effect in replicon assay. A triphosphate of the 6-benzylpurine nucleoside did not inhibit HCV RNA polymerase.(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) were involved in the experimental procedure.

(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

Ramasamy, Kanda S.;Tam, Robert C.;Bard, Josie;Averett, Devron R. published 《Monocyclic L-Nucleosides with Type 1 Cytokine-Inducing Activity》. The research results were published in《Journal of Medicinal Chemistry》 in 2000.HPLC of Formula: 144490-03-9 The article conveys some information:

A series of 1,2,4-triazole L-nucleosides were synthesized and evaluated for their ability to stimulate type 1 cytokine production by activated human T cells in direct comparison to the known active agent ribavirin. Among the compounds prepared, 1-β-L-ribofuranosyl-1,2,4-triazole-3-carboxamide (ICN 17261) was found to be the most uniformly potent compound Conversion of the 3-carboxamide group to a carboxamidine functionality resulted in 1-β-L-ribofuranosyl-1,2,4-triazole-3-carboxamidine hydrochloride, which induced cytokine levels comparable to ICN 17261 for two of the three type 1 cytokines examined Modification of the carbohydrate moiety of ICN 17261 provided compounds of reduced activity. Significantly, ICN 17261 offers interesting immunomodulatory potential for the treatment of diseases where type 1 cytokines play an important role. 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

Jiangseubchatveera, Nadechanok;Bouillon, Marc E.;Liawruangrath, Boonsom;Liawruangrath, Saisunee;Nash, Robert J.;Pyne, Stephen G. published 《Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities》 in 2013. The article was appeared in 《Organic & Biomolecular Chemistry》. They have made some progress in their research.Category: tetrahydrofurans The article mentions the following:

A concise synthesis of (-)-steviamine is reported along with the synthesis of its analogs 10-nor-steviamine, 10-nor-ent-steviamine and 5-epi-ent-steviamine. These compounds were tested against twelve glycosidases (at 143 μg mL^-1 concentrations) and were found to have in general poor inhibitory activity against most enzymes. The 10-nor analogs however, showed 50-54% inhibition of α-l-rhamnosidase from Penicillium decumbens while one of these, 10-nor-steviamine, showed 51% inhibition of N-acetyl-β-d-glucosaminidase (from Jack bean) at the same concentration (760 μM). 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

Product Details of 144490-03-9In 2005, Zhang, Pingsheng;Dong, Zhiming E.;Cleary, Thomas P. published 《Synthesis of Methyl 1-(2,3,5-Tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate from L-Ribose: From a Laboratory Procedure to a Manufacturing Process》. 《Organic Process Research & Development》published the findings. The article contains the following contents:

A two-step manufacturing process for Me 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (I) was developed via methanolysis, acetylation, acetolysis, and coupling reactions. In step 1, L-ribose was converted to a β/α mixture of 1,2,3,5-tetra-O-acetyl-L-ribofuranoses (II). The step contained four chem. transformations and was completed in “one-pot” in approx. 95% yield. The crude step 1 product was reacted with Me 1,2,4-triazole-3-carboxylate in step 2 to produce I. The successful utilization of both isomers II in step 2 offered advantages of higher overall yield and a much simplified process by eliminating the isolation of pure I. The process was successfully scaled up to the pilot plant and subsequently in a manufacturing campaign using com. production facilities. The experimental procedure involved many compounds, such as (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 Product Details 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, Zhen-Dan;Yang, Bing-Hui;Wu, Yu-Lin published 《A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides》 in 2002. The article was appeared in 《Tetrahedron》. They have made some progress in their research.Name: (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate The article mentions the following:

Using an inexpensive D-galactose from the chiral pool, L-deoxyribose, L-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis of L-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-L-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis of L-ribose, the key step of inversion of the 2-hydroxy group in the same substrate was carried out by intramol. S_N2 tandem reaction. Then the L-ribosyl donors were submitted to glycosidations according to Vorbruggen’s conditions to give L-ribosides (L-uridine, L-5-fluorouridine, L-iodouridine, L-thymidine, L-puridine, L-adenosine and L-guanosine) in excellent yields.(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) were involved in the experimental procedure.

(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 Name: (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