Heterocyclic Building Blocks-Tetrahydrofuran

Pd(0)/Cu(I)-Mediated Direct Arylation of 2′-Deoxyadenosines: Mechanistic Role of Cu(I) and Reactivity Comparisons with Related Purine Nucleosides was written by Storr, Thomas E.;Baumann, Christoph G.;Thatcher, Robert J.;De Ornellas, Sara;Whitwood, Adrian C.;Fairlamb, Ian J. S.. And the article was included in Journal of Organic Chemistry in 2009.Application In Synthesis of (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol hydrate This article mentions the following:

Pd/Cu-mediated direct arylation of 2′-deoxyadenosine with various aryl iodides provides 8-arylated 2′-deoxyadenosine derivatives in good yields. Following significant reaction optimization, it has been determined that a substoichiometric quantity of piperidine (secondary amine) in combination with cesium carbonate is necessary for effective direct arylation. The general synthetic protocol allows lower temperature direct arylations, which minimizes deglycosylation. The origin of the piperidine effect primarily derives from the in situ generation of Pd(OAc)₂[(CH₂)₅NH]₂. Various copper(I) salts have been evaluated; only CuI provides good yields of the 8-arylated-2′-deoxyadenosines. Copper(I) appears to have a high binding affinity for 2′-deoxyadenosine, which explains the mandatory requirement for stoichiometric amounts of this key component. The conditions are compared with more general direct arylation protocols, e.g., catalytic Pd, ligand, acid additives, which do not employ copper(I). In each case, no detectable arylation of 2′-deoxyadenosine was noted. The conformational preferences of the 8-aryl-2′-deoxyadenosine products have been determined by detailed spectroscopic (NMR) and single crystal X-ray diffraction studies. Almost exclusively, the preferred solution-state conformation was determined to be syn-C2′-endo (ca. 80%). The presence of a 2-pyridyl group at the 8-position further biases the solution-state equilibrium toward this conformer (ca. 88%), due to an addnl. H-bond between H1′ and the pyridyl nitrogen atom. The Pd/Cu catalyst system has been found to be unique for adenosine type substrates, the reactivity of which has been placed into context with the reported direct arylations of related 1H-imidazoles. The reactivity of other purine nucleosides has been assessed, which has revealed that both 2′-deoxyguanosine and guanosine are incompatible with the Pd/Cu-direct arylation conditions. Both substrates appear to hinder catalysis, akin to the established inhibitory effects in Suzuki cross-couplings with arylboronic acids. In the experiment, the researchers used many compounds, for example, (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol hydrate (cas: 16373-93-6Application In Synthesis of (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol hydrate).

(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol hydrate (cas: 16373-93-6) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF), or oxolane, is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. THF can also be synthesized by catalytic hydrogenation of furan. This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced. THF is thus derivable from renewable resources.Application In Synthesis of (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol hydrate

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

Exploring the intracellular pharmacokinetics of the 5-fluorouracil nucleotides during capecitabine treatment was written by Derissen, Ellen J. B.;Jacobs, Bart A. W.;Huitema, Alwin D. R.;Rosing, Hilde;Schellens, Jan H. M.;Beijnen, Jos H.. And the article was included in British Journal of Clinical Pharmacology in 2016.Formula: C9H11FN2O5 This article mentions the following:

Aim : Three intracellularly formed metabolites are responsible for the antineoplastic effect of capecitabine: 5-fluorouridine 5′-triphosphate (FUTP), 5-fluoro-2′-deoxyuridine 5′-triphosphate (FdUTP), and 5-fluoro-2′-deoxyuridine 5′-monophosphate (FdUMP). The objective of this study was to explore the pharmacokinetics of these intracellular metabolites during capecitabine treatment. Methods : Serial plasma and peripheral blood mononuclear cell (PBMC) samples were collected from 13 patients treated with capecitabine 1000 mg QD (group A) and eight patients receiving capecitabine 850 mg m^-2 BID for fourteen days, every three weeks (group B). Samples were collected on day 1 and, for four patients of group B, also on day 14. The capecitabine and 5-fluorouracil (5-FU) plasma concentrations and intracellular metabolite concentrations were determined using LC-MS/MS. Pharmacokinetic parameters were estimated using non-compartmental anal. Results : Only FUTP could be measured in the PBMC samples. The FdUTP and FdUMP concentrations were below the detection limits (LOD). No significant correlation was found between the plasma 5-FU and intracellular FUTP exposure. The FUTP concentration-time profiles demonstrated considerable inter-individual variation and accumulation of the metabolite in PBMCs. FUTP levels ranged between <LOD and 1.0 μM on day 1, and from 0.64 to 14 μM on day 14. The area under the FUTP concentration-time curve was significantly increased on day 14 of the treatment compared to day 1 (mean ± SD: 28 ± 19 μM h vs. 2.0 ± 1.9 μM h). Conclusions : To our knowledge, this is the first time that intracellular FUTP concentrations were measured in patients treated with capecitabine. During 14 days of treatment with capecitabine twice daily, intracellular accumulation of FUTP occurs. In the experiment, the researchers used many compounds, for example, 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione (cas: 3094-09-5Formula: C9H11FN2O5).

1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione (cas: 3094-09-5) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Formula: C9H11FN2O5

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

Synthesis of 5-fluoro-4-deoxy-β-L-uridine was written by Dong, Chun-Hong;Qi, Xiu-Xiang;Yu, Xue-Jun;Chang, Jun-Biao. And the article was included in Gaodeng Xuexiao Huaxue Xuebao in 2004.Category: tetrahydrofurans This article mentions the following:

The title compound was prepared in 10 steps starting from L-xylose via condensation of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose with silylated 5-fluorouracil. The structures of compounds were identified by the MS, UV, IR, ¹H NMR spectra and elemental analyses. In the experiment, the researchers used many compounds, for example, (3aS,5S,6R,6aS)-5-(Hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 114861-22-2Category: tetrahydrofurans).

(3aS,5S,6R,6aS)-5-(Hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 114861-22-2) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF) is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II). Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Category: tetrahydrofurans

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

Ammonium ions enhance proteolytic activation of adenylate cyclase and decrease its sensitivity to inhibition by “P”-site agonists was written by Yeung, Siu Mei Helena;Shoshani, Ilana;Stuebner, Dorothee;Johnson, Roger A.. And the article was included in Archives of Biochemistry and Biophysics in 1989.COA of Formula: C10H13N5O2 This article mentions the following:

A detergent-dispersed adenylate cyclase from rat brain was used to study the effects of ammonium salts and polyamines on the proteolytic activation of the enzyme by a sperm protease and on the sensitivity of adenylate cyclase to inhibition via its P-site. A purified preparation of a trypsinlike serine protease from bovine sperm was used to activate solubilized adenylate cyclase in the presence of guanosine 5′-O-(3-thiotriphosphate (GTPγS). The proteolytically activated form of adenylate cyclase was particularly sensitive to further activation by NH₄HCO₃. The activation by NH₄HCO₃ was due to the NH₄⁺ cation and was characterized by an increased V_max and by a decreased sensitivity of adenylate cyclase to inactivation by elevated concentrations of the sperm protease or by trypsin. NH₄Cl and (NH₄)₂SO₄ also caused biphasic effects on adenylate cyclase, that mimicked but were less effective than those caused by NH₄HCO₃. Consistent with observations of others, adenylate cyclase activity was enhanced by NH⁺ whether in the presence of reversible (Mn²⁺) or irreversible (GTPγS) activators. Mn²⁺– and GTPγS-stimulated activities were similarly optimally enhanced by 30 mM (NH₄)₂SO₄ and by 30-150 mM NH₄Cl or NH₄HCO₃. NH₄⁺ did not increase the activity of the purified catalytic unit. Moreover, the effect of NH₄⁺ was not accompanied by an increased rate of activation by GTPγS, suggesting that the activation of G_s (guanine nucleotide-dependent stimulatory component) may not be the primary cause of stimulation by ammonium salts. Several polyamines at millimolar concentrations blocked the stimulatory effect of NH₄⁺. This was observed when adenylate cyclase was activated by Mn²⁺, but not when it was activated by GTPγS or by the sperm protease plus GTPγS. The inhibitory effect of polyamines was not due to the formation of a complex with ATP. Both the increase in V_max of the Mn²⁺-stimulated enzyme by NH₄⁺ and the decrease in V_max caused by spermine were accompanied by an increase in the apparent K_m for MnATP. Spermine increased the IC₅₀ for inhibition of Mn²⁺-activated adenylate cyclase by 2′,5′-dideoxyadenosine (2′,5′-ddAdo) from 0.75 to 4.6 μM, consistent with the idea that increased sensitivity of P-site-mediated inhibition is associated with increased enzyme activity. In contrast, activation of Mn²⁺-stimulated adenylate cyclase by 30 mM (NH₄)₂SO₄ also reduced sensitivity to inhibition by 2′,5′-ddAdo (IC₅₀ 1.1 μM). This decreased sensitivity to inhibition by 2′,5′-ddAdo induced by NH₄⁺ was also observed on GTPS-activated or proteolytically activated adenylate cyclase. Thus, activation of adenylate cyclase by ammonium salts may be due to an effect on the conformation and(or) stability of the active form of the enzyme, leading to increased enzyme activity as well as to decreased proteolytic inactivation. In the experiment, the researchers used many compounds, for example, (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol (cas: 6698-26-6COA of Formula: C10H13N5O2).

(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol (cas: 6698-26-6) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF), or oxolane, is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.COA of Formula: C10H13N5O2

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

Sensitive high-throughput assays for tumour burden reveal the response of a Drosophila melanogaster model of colorectal cancer to standard chemotherapies was written by Adams, Jamie;Casali, Andreu;Campbell, Kyra. And the article was included in International Journal of Molecular Sciences in 2021.Related Products of 3094-09-5 This article mentions the following:

Drosophila melanogaster (Drosophila) models of cancer are emerging as powerful tools to investigate the basic mechanisms underlying tumor progression and identify novel therapeutics. Rapid and inexpensive, it is possible to carry out genetic and drug screens at a far larger scale than in vertebrate organisms. Such whole-organism-based drug screens permits assessment of drug absorption and toxicity, reducing the possibility of false positives. Activating mutations in the Wnt and Ras signalling pathways are common in many epithelial cancers, and when driven in the adult Drosophila midgut, it induces aggressive intestinal tumor-like outgrowths that recapitulate many aspects of human colorectal cancer (CRC). Here we have taken a Drosophila CRC model in which tumorous cells are marked with both GFP and luciferase reporter genes, and developed novel high-throughput assays for quantifying tumor burden. Leveraging these assays, we find that the Drosophila CRC model responds rapidly to treatment with standard CRC-drugs, opening the door to future rapid genetic and drug screens. In the experiment, the researchers used many compounds, for example, 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione (cas: 3094-09-5Related Products of 3094-09-5).

1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione (cas: 3094-09-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.Related Products of 3094-09-5

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

Nucleic Acid Related Compounds. 118. Nonaqueous Diazotization of Aminopurine Derivatives. Convenient Access to 6-Halo- and 2,6-Dihalopurine Nucleosides and 2′-Deoxynucleosides with Acyl or Silyl Halides was written by Francom, Paula;Robins, Morris J.. And the article was included in Journal of Organic Chemistry in 2003.Category: tetrahydrofurans This article mentions the following:

Treatment of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloropurine with TMS-Cl and benzyltriethylammonium nitrite (BTEA-NO₂) in dichloromethane gave the crystalline 2,6-dichloropurine nucleoside I (R = OAc, X = Y = Cl), and acetyl chloride/BTEA-NO₂ was equally effective (∼85%, without chromatog.). TMS-Br/tert-Bu nitrite/dibromomethane gave crystalline 2-bromo-6-chloro analog I (R = OAc, X = Br, Y = Cl) (85%). (Chloro or bromo)-dediazoniation of 3′,5′-di-O-acetyl-2′-deoxyadenosine gave chloro I (R = X = H, Y = Cl) (63%) or bromo I (R = X = H, Y = Br) (80%) purine deoxynucleosides, and 2′,3′,5′-tri-O-acetyladenosine was converted into the 6-chloropurine nucleoside I (R = OAc, X = H, Y = Cl) (71%). In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6Category: tetrahydrofurans).

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. Tetrahydrofuran can also be produced, or synthesised, via catalytic hydrogenation of furan. This process involves converting certain sugars into THF by digesting to furfural. An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.Category: tetrahydrofurans

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

Spectrofluorimetric method for the determination of alfuzosin and flavoxate hydrochlorides in pharmaceuticals and biological fluids was written by Razeq, Sawsan A.. And the article was included in Egyptian Journal of Analytical Chemistry in 2008.Electric Literature of C19H28ClN5O4 This article mentions the following:

A simple and sensitive spectrofluorimetric method was developed to determine alfuzosin-HCl and flavoxate-HCl. Maximum fluorescence intensity was achieved in pure water at 388 nm and 375 nm using λex 244 nm and 240 nm for alfuzosin-HCl and flavoxate-HCl, resp. The optimum exptl. parameters such as solvent, micelle-enhancement, and pH were evaluated. Good correlations were obtained between the fluorescence intensity and concentration in the ranges of 2.5-30 ng/mL for alfuzosin and 1-6 μg/mL for flavoxate-HCl. The suggested method was successfully applied to estimate the 2 drugs in their tablets with average recoveries of 99.2 and 99.8%, resp. These results were found to agree with those of reference methods. The method also retained its accuracy and precision when applied to determine alfuzosin-HCl in spiked blood serum or urine as judged by an average recovery of 95.4 or 100.1%, resp. Furthermore, the method was validated according to the International Conference on Harmonization. In the experiment, the researchers used many compounds, for example, N-(3-((4-Amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino)propyl)tetrahydrofuran-2-carboxamide hydrochloride (cas: 81403-68-1Electric Literature of C19H28ClN5O4).

N-(3-((4-Amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino)propyl)tetrahydrofuran-2-carboxamide hydrochloride (cas: 81403-68-1) belongs to tetrahydrofuran derivatives. Tetrahydrofuran and dihydrofuran form the basic structural unit of many naturally occurring scaffolds like gambieric acid A and ciguatoxin, goniocin, and some biologically active molecules. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Electric Literature of C19H28ClN5O4

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

Feedback inhibition of asparate transcarbamylase in liver and in hepatoma was written by Bresnick, Edward. And the article was included in Cancer Research in 1962.SDS of cas: 10356-76-0 This article mentions the following:

Partially purified asparate transcarbamylase (I) from rat liver, Morris hepatoma 5123-A or D, Hepatoma 7800, and Novikoff hepatoma, was shown to be inhibited by pyrimidine deoxyribonucleosides and deoxyribonucleotides. The pyrimidine analogs, 5-bromo-2′-deoxyuridine, 5-bromouridine, 5-bromo-2′-deoxycytidine, 5-fluoro-2′-deoxyuridine, 5-fluorouridine, 5-fluoro-2′-deoxycytidine, 5-iodo-2-deoxyuridine, also inhibited enzymic activity. The most effective inhibitors were 2′-deoxyadenosine 5′-monophosphate (or 2′-deoxyguanosine 5′-monophosphate) and 2′-deoxyadenosine (II) or 2′-deoxyguanosine (III). I was identical in liver and in the hepatomas by pH optimum, K_m values for carbamoyl phosphate and asparate, V_maximum degree of inhibition by Cu⁺⁺, by the pyrimidines, and by the inhibition constants Neg. feedback inhibition of pyrimidine biosynthesis occurs in hepatomas as well as in liver, and to the same extent. Furthermore, the control of I by II (or III) may play a significant role in vivo. In the experiment, the researchers used many compounds, for example, 4-Amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 10356-76-0SDS of cas: 10356-76-0).

4-Amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 10356-76-0) belongs to tetrahydrofuran derivatives. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.SDS of cas: 10356-76-0

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

Decarboxylative C-C and C-N Bond Formation by Ligand-Accelerated Iron Photocatalysis was written by Feng, Guangshou;Wang, Xiaofei;Jin, Jian. And the article was included in European Journal of Organic Chemistry in 2019.Electric Literature of C5H8O3 This article mentions the following:

A mild and effective protocol for decarboxylative C-C and C-N bond formation through iron photocatalysis was achieved. The carboxylic acids underwent radical decarboxylation in the presence of Fe₂(SO₄)₃ and di-(2-picolyl)amine under visible light irradiation The resulting alkyl radicals then reacted with Michael acceptors or azodicarboxylates to furnish the adducts. In the experiment, the researchers used many compounds, for example, Tetrahydrofuran-2-carboxylic acid (cas: 16874-33-2Electric Literature of C5H8O3).

Tetrahydrofuran-2-carboxylic acid (cas: 16874-33-2) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF), or oxolane, is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. Commercial tetrahydrofuran contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although tetrahydrofuran is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.Electric Literature of C5H8O3

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

HIV pre-exposure prophylaxis for women and infants prevents vaginal and oral HIV transmission in a preclinical model of HIV infection was written by Kovarova, Martina;Shanmugasundaram, Uma;Baker, Caroline E.;Spagnuolo, Rae Ann;De, Chandrav;Nixon, Christopher C.;Wahl, Angela;Garcia, J. Victor. And the article was included in Journal of Antimicrobial Chemotherapy in 2016.Electric Literature of C12H12FN5O3 This article mentions the following:

Background: Approx. 1.5 million HIV-pos. women become pregnant annually. Without treatment, up to 45% will transmit HIV to their infants, primarily through breastfeeding. These numbers highlight that HIV acquisition is a major health concern for women and children globally. They also emphasize the urgent need for novel approaches to prevent HIV acquisition that are safe, effective and convenient to use by women and children in places where they are most needed. Methods: 4′-Ethynyl-2-fluoro-2′-deoxyadenosine, a potent NRTI with low cytotoxicity, was administered orally to NOD/SCID/γc/ mice and to bone marrow/liver/thymus (BLT) humanized mice, a preclin. model of HIV infection. HIV inhibitory activity in serum, cervicovaginal secretions and saliva was evaluated 4 h after administration. 4′-Ethynyl-2-fluoro-2′-deoxyadenosine’s ability to prevent vaginal and oral HIV transmission was evaluated using highly relevant transmitted/founder viruses in BLT mice. Results: Strong HIV inhibitory activity in serum, cervicovaginal secretions and saliva obtained from animals after a single oral dose of 4′-ethynyl-2-fluoro-2′-deoxyadenosine (10 mg/kg) demonstrated efficient drug penetration into relevant mucosal sites. A single daily oral dose of 4′-ethynyl-2-fluoro-2′-deoxyadenosine resulted in efficient prevention of vaginal and oral HIV transmission after multiple high-dose exposures to transmitted/founder viruses in BLT humanized mice. Conclusions: Our data demonstrated that 4′-ethynyl-2-fluoro-2′-deoxyadenosine efficiently prevents both vaginal and oral HIV transmission. Together with 4′-ethynyl-2-fluoro-2′-deoxyadenosine’s relatively low toxicity and high potency against drug-resistant HIV strains, these data support further clin. development of 4′-ethynyl-2-fluoro-2′-deoxyadenosine as a potential pre-exposure prophylaxis agent to prevent HIV transmission in women and their infants. In the experiment, the researchers used many compounds, for example, (2R,3S,5R)-5-(6-Amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol (cas: 865363-93-5Electric Literature of C12H12FN5O3).

(2R,3S,5R)-5-(6-Amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol (cas: 865363-93-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF) is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II). Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Electric Literature of C12H12FN5O3

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