Day: September 16, 2022

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

COA of Formula: C9H10O3《Preparation and Structure of di-exo-Condensed Norbornane Heterocycles》 was published in 2004. The authors were Miklos, Ferenc;Hetenyi, Anasztazia;Sohar, Pal;Stajer, Geza, and the article was included in《Monatshefte fuer Chemie》. The author mentioned the following in the article:

Cyclization of di-exo-aroylnorbornanecarboxylic acid with bidentate nucleophiles (hydrazine, o-phenylenediamine, o-aminophenol, alkylenediamines, and amino alcs.) yielded heterotri-, tetra-, and pentacycles, such as I (R = β-C₆H₄-4-Me, X = S; R = α-C₆H₄-4-Me, X = O, NH) and II [R = C₆H₄-4-Me, R¹ = H, X = O, Y = (CH₂)_n, n = 1, 2; R = C₆H₄-4-Me, R¹ = H, X = NH, Y = (CH₂)_n, n = 1, 2, 3; R = C₆H₄-4-Me, R¹ = Me, X = NH, Y = (CH₂)_n, n = 1]. The structures of the heterocyclics were established by means of NMR spectroscopy, with the application of HMQC, HMBC, DEPT, DIFFNOE, and COSY methods.(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

Brouwer, H.;Stothers, J. B.;Tan, C. T. published 《Carbon-13 NMR studies. Part 66. Carbon-13 spectra of several methyl, hydroxymethyl, and carboxylic acid derivatives of bicyclo[2.2.1]heptane and bicyclo[2.2.2]octane》 in 1977. The article was appeared in 《Organic Magnetic Resonance》. They have made some progress in their research.Name: (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione The article mentions the following:

The ¹³C NMR spectra of 56 norbornanes, -enes, bicyclo[2.2.2]octanes, and -octenes were determined to study the stereochem. effects of neighboring substituents on the C shieldings. Use of these rigid skeletons enabled detailed examination of a variety of substituent orientations. The deviation of the observed shieldings from those predicted by simple additivity followed patterns useful for stereochem. assignments in related systems. 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.Name: (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

Safety of (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione《Succinimide derivatives. II. Synthesis and antipsychotic activity of N-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-1,2-cis-cyclohexanedicarboximide (SM-9018) and related compounds》 was published in 1995. The authors were Ishizumi, Kikuo;Kojima, Atsuyuki;Antoku, Fujio;Saji, Ikutaro;Yoshigi, Mayumi, and the article was included in《Chemical & Pharmaceutical Bulletin》. The author mentioned the following in the article:

Cyclic imides bearing ω-(4-benzisothiazol-3-yl-1-piperazinyl)alkyl moieties were synthesized and tested for antipsychotic activity. The in vitro binding affinities of these compounds were examined for dopamine 2 (D₂) and serotonin 2 (5-HT₂) receptor sites. Structure-activity relationships within these series are discussed. One of these compounds, namely, SM-9018 (I), was found to be more potent and more selective in vivo than tiospirone in its antipsychotic activity. 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.Safety 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

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

O’Brien, Erin M.;Bercot, Eric A.;Rovis, Tomislav published 《Decarbonylative Cross-Coupling of Cyclic Anhydrides: Introducing Stereochemistry at an sp³ Carbon in the Cross-Coupling Event》. The research results were published in《Journal of the American Chemical Society》 in 2003.Quality Control of (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione The article conveys some information:

Treatment of cyclic anhydrides with stoichiometric amounts of nickel-neocuproine complex generates alkylcarboxylato-nickelalactones upon extrusion of CO. These metallacycles undergo cross-coupling with arylzinc reagents. The generated CO is sequestered in situ by a nickel-dppb complex. The overall sequence effects a secondary sp³(electrophile)-sp²(nucleophile) cross-coupling and allows for control of stereochem. during the bond-forming 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.Quality Control 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

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