Jensen, Pernille R.’s team published research in ACS Sustainable Chemistry & Engineering in 2020 | CAS: 19444-84-9

3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9) may be employed as starting reagent in the synthesis of series of seco-pseudonucleoside synthons via aminolysis. It may be employed as starting reagent in the synthesis of enantiomerically pure orthogonally protected δ-azaproline, via Mitsunobu reaction.SDS of cas: 19444-84-9

《Visualization of Pathway Usage in an Extended Carbohydrate Conversion Network Reveals the Impact of Solvent-Enabled Proton Transfer》 was written by Jensen, Pernille R.; Knudsen, Rikke K.; Meier, Sebastian. SDS of cas: 19444-84-9 And the article was included in ACS Sustainable Chemistry & Engineering on August 17 ,2020. The article conveys some information:

Bio-sourced mols. should increasingly contribute to meeting societal demands for energy and chems., while reducing net carbon dioxide release and the dependence on fossil resources. Especially oxygenated chems. can be derived from carbohydrates, and the conversion of carbohydrates in protic and nonprotic solvents has attracted considerable interest. Here, we probe chemocatalytic carbohydrate conversion in a time-resolved manner using quant. in situ NMR spectroscopy. A core reaction network in the carbohydrate conversion by Sn(IV) in nonprotic solvents is followed by identifying and quant. tracking 10 chems. with more than 70 at. sites. In situ anal. yields nine rate constants and shows that (co)solvents with labile protons strongly affect tautomerization kinetics and product distributions at an upstream branch point of the reaction network. Solvent-enabled tautomerization and the ensuing accumulation of reactive 1,2-dicarbonyl compounds can thus be key factors influencing reaction kinetics and atom economy in carbohydrate conversion. A reaction network for carbohydrate valorization was observed, revealing the impact of solvent protons on the desired process and on aggregation and degradation reactions. In the experimental materials used by the author, we found 3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9SDS of cas: 19444-84-9)

3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9) may be employed as starting reagent in the synthesis of series of seco-pseudonucleoside synthons via aminolysis. It may be employed as starting reagent in the synthesis of enantiomerically pure orthogonally protected δ-azaproline, via Mitsunobu reaction.SDS of cas: 19444-84-9

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

Kiddane, Anley Teferra’s team published research in Current Issues in Molecular Biology in 2022 | CAS: 19444-84-9

3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9) is a 5-membered cyclic ester. It was obtained via tin-conversion of biomass-derived 1,3-dihydroxyacetone (DHA) and formaldehyde. And it may be employed as starting reagent in the synthesis of series of seco-pseudonucleoside synthons via aminolysis.Application In Synthesis of 3-Hydroxydihydrofuran-2(3H)-one

In 2022,Current Issues in Molecular Biology included an article by Kiddane, Anley Teferra; Kang, Min-Jae; Ho, Truc Cong; Getachew, Adane Tilahun; Patil, Maheshkumar Prakash; Chun, Byung-Soo; Kim, Gun-Do. Application In Synthesis of 3-Hydroxydihydrofuran-2(3H)-one. The article was titled 《Anticancer and Apoptotic Activity in Cervical Adenocarcinoma HeLa Using Crude Extract of Ganoderma applanatum》. The information in the text is summarized as follows:

Cancer is currently one of the foremost health challenges and a leading cause of death worldwide. Cervical cancer is caused by cofactors, including oral contraceptive use, smoking, multiparity, and HIV infection. One of the major and considerable etiologies is the persistent infection of the oncogenic human papilloma virus. G. applanatum is a valuable medicinal mushroom that has been widely used as a folk medicine for the treatment and prevention of various diseases. In this study, we obtained crude extract from G. applanatum mushroom with a subcritical water extraction method; cell viability assay was carried out and the crude extract showed an antiproliferative effect in HeLa cells with IC50 of 1.55 ± 0.01 mg/mL; however, it did not show any sign of toxicity in HaCaT. Protein expression was detected by Western blot, stability of IκBα and downregulation of NFκB, IKKα, IKKβ, p-NFκB-65(Ser 536) and p-IKKα/β(Ser 176/180), suggesting loss of survival in a dose-dependent manner. RT-qPCR revealed RNA/mRNA expression; fold changes of gene expression in Apaf-1, caspase-3, cytochrome-c, caspase-9, Bax and Bak were increased, which implies apoptosis, and NFκB was decreased in a dose-dependent manner. DNA fragmentation was seen in the treatment groups as compared to the control group using gel electrophoresis. Identification and quantification of compounds were carried out by GC-MS and HPLC, resp.; 2(5H)furanone with IC50 of 1.99 ± 0.01 μg/mL could be the responsible anticancer compound In conclusion, these findings suggest the potential use of the crude extract of G. applanatum as a natural source with anticancer activity against cervical cancer. In addition to this study using 3-Hydroxydihydrofuran-2(3H)-one, there are many other studies that have used 3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9Application In Synthesis of 3-Hydroxydihydrofuran-2(3H)-one) was used in this study.

3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9) is a 5-membered cyclic ester. It was obtained via tin-conversion of biomass-derived 1,3-dihydroxyacetone (DHA) and formaldehyde. And it may be employed as starting reagent in the synthesis of series of seco-pseudonucleoside synthons via aminolysis.Application In Synthesis of 3-Hydroxydihydrofuran-2(3H)-one

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

James-Okoro, Paula-Peace O.’s team published research in World News of Natural Sciences in 2021 | CAS: 19444-84-9

3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9) is a 5-membered cyclic ester. It was obtained via tin-conversion of biomass-derived 1,3-dihydroxyacetone (DHA) and formaldehyde. And it may be employed as starting reagent in the synthesis of series of seco-pseudonucleoside synthons via aminolysis.Recommanded Product: 3-Hydroxydihydrofuran-2(3H)-one

In 2021,World News of Natural Sciences included an article by James-Okoro, Paula-Peace O.; Iheagwam, Franklyn N.; Sholeye, Mariam I.; Umoren, Itoroobong A.; Adetuyi, Babatunde O.; Ogundipe, Adebanke E.; Braimah, Adefoyeke A.; Adekunbi, Tobi S.; Ogunlana, Oluseyi E.; Ogunlana, Olubanke O.. Recommanded Product: 3-Hydroxydihydrofuran-2(3H)-one. The article was titled 《Phytochemical and in vitro antioxidant assessment of Yoyo bitters》. The information in the text is summarized as follows:

In this paper, herbal bitters are widely used due to their numerous acclaimed health benefits in many Nigerian homes; however, many have not been subjected to scientific scrutiny. The aim of this study was to determine the phytochem. composition and antioxidant capacity of a non-alc. polyherbal formulation, Yoyo bitters, towards validating its broad pharmacol. claims. The phytochem. components of Yoyo bitters were ascertained by phytochem. screening assays and gas chromatog.-mass spectrometry (GC-MS). The antioxidant activity was investigated in vitro using 2,2-diphenyl-1-picryhydrazyl (DPPH) radical, hydrogen peroxide (H2O2) scavenging activity, total antioxidant capacity (TAC) and ferric reducing antioxidant power (FRAP) assays. Qual. phytochem. anal. of Yoyo bitters showed the presence of saponins, tannins, flavonoids, terpenoids, cardiac glycosides and anthocyanins. The total phenols, flavonoids, flavanols, tannins and carotenoids content were 14.741 ± 0.64 mg GAE/mL, 0.152 ± 0.01 mg RE/mL, 0.437 ± 0.02 mg RE/mL, 0.368 ± 0.04 mg TAE/mL and 0.016 ± 0.00 mg CAE/mL resp. GC-MS chromatogram revealed the presence of forty-three (43) phytochem. compounds with D-allose (41.81%), 1,6-anhydro-beta-D-glucofuranose (24.15%), 5-hydroxymethylfurfural (8.02%) and Z-6-pentadecen-1-ol acetate (3.50%) as the most abundant constituents. Yoyo bitters demonstrated effective antioxidant activity against DPPH and H2O2 with IC50 values of 0.492 mg/mL and 0.629 mg/mL resp. compared to ascorbic acid of 0.161 mg/mL and 0.130 mg/mL resp. Total antioxidant capacity and ferric reducing antioxidant power of Yoyo bitters were 0.432 mg AAE/mL and 2.236 mg AAE/mL resp. This study validates the antioxidant capacity of Yoyo bitters and provides chem. basis for its acclaimed pharmacol. actions.3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9Recommanded Product: 3-Hydroxydihydrofuran-2(3H)-one) was used in this study.

3-Hydroxydihydrofuran-2(3H)-one(cas: 19444-84-9) is a 5-membered cyclic ester. It was obtained via tin-conversion of biomass-derived 1,3-dihydroxyacetone (DHA) and formaldehyde. And it may be employed as starting reagent in the synthesis of series of seco-pseudonucleoside synthons via aminolysis.Recommanded Product: 3-Hydroxydihydrofuran-2(3H)-one

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

Cas: 14166-28-0 was involved in experiment | Monatshefte fuer Chemie 2004

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.

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

Application of cas: 14166-28-0 | Albers, Thomas et al. published an article in 1996

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.Application of 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Albers, Thomas;Biagini, Stefano C. G.;Hibbs, David E.;Hursthouse, Michael B.;Malik, K. M. Abdul;North, Michael;Uriarte, Eugenio;Zagotto, Guiseppe published 《Desymmetrization of meso-anhydrides utilizing (S)-proline derivatives》 in 1996. The article was appeared in 《Synthesis》. They have made some progress in their research.Application of 14166-28-0 The article mentions the following:

Meso-anhydrides derived from norbornanes and norbornenes undergo an asym. ring opening upon treatment with (S)-proline derivatives to give amido acids with moderate to excellent enantiomeric excesses. A cyclopropane derived anhydride was also desymmetrized in this way, while cyclohexyl derived anhydrides gave a 1:1 mix. of diastereomers. The origin of the desymmetrization is explained by a model based on steric interactions in the transition state. 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.Application of 14166-28-0 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

Explore more uses of cas: 14166-28-0 | Journal of Molecular Modeling

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.Related Products of 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Molina-Espiritu, Moyocoyani;Esquivel, Rodolfo O.;Kohout, Miroslav;Angulo, Juan Carlos;Dobado, Jose A.;Dehesa, Jesus S.;LopezRosa, Sheila;Soriano-Correa, Catalina published 《Insight into the informational-structure behavior of the Diels-Alder reaction of cyclopentadiene and maleic anhydride》. The research results were published in《Journal of Molecular Modeling》 in 2014.Related Products of 14166-28-0 The article conveys some information:

The course of the Diels-Alder reactions of cyclopentadiene and maleic anhydride were studied. Two reaction paths were modelled: endo- and exo-selective paths. All structures within the transient region were characterized and analyzed by means of geometrical descriptors, physicochem. parameters and information-theor. measures in order to observe the linkage between chem. behavior and the carriage of information. We have shown that the information-theor. characterization of the chem. course of the reaction is in complete agreement with its phenomenol. behavior in passing from reactants to products. In addition, we were able to detect the main differences between the two reaction mechanisms. This type of informational anal. serves to provide tools to help understand the chem. reactivity of the two simplest Diels-Alder reactions, which permits the establishment of a connection between the quantum changes that mol. systems exert along reaction coordinates and standard physicochem. phenomenol. In the present study, we have shown that every reaction stage has a family of subsequent structures that are characterized not solely by their phenomenol. behavior but also by informational properties of their electronic d. distribution (localizability, order, uniformity). Moreover, we were able to describe the main differences between endo-adduct and exo-adduct pathways. With the advent of new exptl. techniques, it is in principle possible to observe the structural changes in the transient regions of chem. reactions. Indeed, through this work we have provided the theor. concepts needed to unveil the concurrent processes associated with chem. reactions. 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.Related Products of 14166-28-0 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

Cas: 14166-28-0 was involved in experiment | Journal of Organic Chemistry 1982

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.

Canonne, Persephone;Belanger, Denis;Lemay, Gilles published 《Novel synthesis of five- and six-membered spiro γ-lactones in rigid bicyclic systems》. The research results were published in《Journal of Organic Chemistry》 in 1982.Name: (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione The article conveys some information:

The reaction of bis(bromomagnesio)alkanes with bridged tricyclic endo– and exo-dicarboxylic anhydrides and their dihydro derivatives provides a general and versatile route to corresponding tricyclic spiro γ-butanolides. Further extension of this methodol. to the dianhydride of bicyclo[2.2.2]octene showed appreciable regioselectivity. The subsequent transformation of spiro γ-lactones into 4-spiro-2-butenolides by retro-Diels-Alder reaction has provided a simple and convenient synthesis of these mols. Proton and 13C NMR spectra are reported for most of the compounds(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.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

Cas: 14166-28-0 | Chen, Tie-Gen et al. made new progress in 2018

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.Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Chen, Tie-Gen;Barton, Lisa M.;Lin, Yutong;Tsien, Jet;Kossler, David;Bastida, Inaki;Asai, Shota;Bi, Cheng;Chen, Jason S.;Shan, Mingde;Fang, Hui;Fang, Francis G.;Choi, Hyeong-wook;Hawkins, Lynn;Qin, Tian;Baran, Phil S. published 《Building C(sp3)-rich complexity by combining cycloaddition and C-C cross-coupling reactions》. The research results were published in《Nature (London, United Kingdom)》 in 2018.Formula: C9H10O3 The article conveys some information:

Prized for their ability to rapidly generate chem. complexity by building new ring systems and stereocentres, cycloaddition reactions have featured in numerous total syntheses and are a key component in the education of chem. students. Similarly, carbon-carbon (C-C) cross-coupling methods are integral to synthesis because of their programmability, modularity and reliability. Within the area of drug discovery, an overreliance on cross-coupling has led to a disproportionate representation of flat architectures that are rich in carbon atoms with orbitals hybridized in an sp2 manner. Despite the ability of cycloadditions to introduce multiple carbon sp3 centers in a single step, they are less used. This is probably because of their lack of modularity, stemming from the idiosyncratic steric and electronic rules for each specific type of cycloaddition Here we demonstrate a strategy for combining the optimal features of these two chem. transformations into one simple sequence, to enable the modular, enantioselective, scalable and programmable preparation of useful building blocks, natural products and lead scaffolds for drug discovery. 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.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

Cas: 14166-28-0 was involved in experiment | Organic Reactions (Hoboken, NJ, United States) 1998

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.HPLC of Formula: 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Rickborn, Bruce published 《The retro-Diels-Alder reaction. Part I. C-C dienophiles》. The research results were published in《Organic Reactions (Hoboken, NJ, United States)》 in 1998.HPLC of Formula: 14166-28-0 The article conveys some information:

A review of the article The retro-Diels-Alder reaction. Part I. C-C dienophiles. 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.HPLC of Formula: 14166-28-0 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

Cas: 14166-28-0 was involved in experiment | Journal of Organic Chemistry 1968

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.HPLC of Formula: 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

Moriconi, Emil J.;Crawford, Wheeler C. published 《Reaction of chlorosulfonyl isocyanate with bridge bi- and tricyclic olefins》 in 1968. The article was appeared in 《Journal of Organic Chemistry》. They have made some progress in their research.HPLC of Formula: 14166-28-0 The article mentions the following:

The addition of ClSO2NCO to norbornene, norbornadiene, 7-benzoyloxy-, and 7-tert-butoxynorbornadiene, endo-, and exo-dicyclopentadiene, and bicyclo [2.2.2]octene (I) led, in each case, to a single, unrearranged cycloadduct, the N-chlorosulfonyl-β-lactam. A nonconcerted cycloaddition mechanism is proposed. Attempts to form the bis adduct from norbornadiene were unsuccessful. Assignment of the exo configuration to the azetidinone ring in these N-chlorosulfonyl-β-lactams is based predominantly on N.M.R. evidence. Benzenethiol-pyridine reduction of the N-chlorosulfonyl cycloadducts led to the corresponding unsubstituted β-lactams. The ir spectrum of exo-2-p-toluenesulfonamido-3-carboxybicyclo[2.2.1]heptane ultimately prepared from the norbornene cycloadduct expectedly differed from that of the endo isomer prepared by a stereospecific Lossen rearrangement on N-phenylsulfonyloxynorbornane-endo-2,3-dicarboximide. Treatment of N-phenylsulfonyloxynorbornane-exo-2,3-dicarboximide under Lossen conditions failed to yield a rearrangement product, as did the Hofmann reaction on norbornane-exo-2,3-dicarboximide and exo-2-carbomethoxy-3-carboxamidonorbornane. A Lossen rearrangement, however, successfully converted N-sulfonyloxybicyclo[2.2.2]octane-2,3-dicarboximide into 2-amino-3-carboxybicyclo[2.2.2]octane-HCl, identical with the acid hydrolysis product of the β-lactam cyclo-adduct from I. 50 references. 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.HPLC of Formula: 14166-28-0 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