Heterocyclic Building Blocks-Tetrahydrofuran

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

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