Category: Tetrahydrofurans

Active site architecture of an acetyl xylan esterase indicates a novel cold adaptation strategy was written by Zhang, Yi;Ding, Hai-Tao;Jiang, Wen-Xin;Zhang, Xia;Cao, Hai-Yan;Wang, Jing-Ping;Li, Chun-Yang;Huang, Feng;Zhang, Xi-Ying;Chen, Xiu-Lan;Zhang, Yu-Zhong;Li, Ping-Yi. And the article was included in Journal of Biological Chemistry in 2021.Quality Control of (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate This article mentions the following:

SGNH-type acetyl xylan esterases (AcXEs) play important roles in marine and terrestrial xylan degradation, which are necessary for removing acetyl side groups from xylan. However, only a few cold-adapted AcXEs have been reported, and the underlying mechanisms for their cold adaptation are still unknown because of the lack of structural information. Here, a cold-adapted AcXE, AlAXEase, from the Arctic marine bacterium Arcticibacterium luteifluviistationis SM1504^T was characterized. AlAXEase could deacetylate xylooligosaccharides and xylan, which, together with its homologs, indicates a novel SGNH-type carbohydrate esterase family. AlAXEase showed the highest activity at 30 °C and retained over 70% activity at 0 °C but had unusual thermostability with a T_m value of 56 °C. To explain the cold adaptation mechanism of AlAXEase, we next solved its crystal structure. AlAXEase has similar noncovalent stabilizing interactions to its mesophilic counterpart at the monomer level and forms stable tetramers in solutions, which may explain its high thermostability. However, a long loop containing the catalytic residues Asp200 and His203 in AlAXEase was found to be flexible because of the reduced stabilizing hydrophobic interactions and increased destabilizing asparagine and lysine residues, leading to a highly flexible active site. Structural and enzyme kinetic analyses combined with mol. dynamics simulations at different temperatures revealed that the flexible catalytic loop contributes to the cold adaptation of AlAXEase by modulating the distance between the catalytic His203 in this loop and the nucleophilic Ser32. This study reveals a new cold adaptation strategy adopted by the thermostable AlAXEase, shedding light on the cold adaptation mechanisms of AcXEs. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (cas: 126-14-7Quality Control of (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate).

(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (cas: 126-14-7) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Tetrahydrofuran (THF) is primarily used as a precursor to polymers including for surface coating, adhesives, and printing inks.Quality Control of (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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

Carbohydrates, volatile and phenolic compounds composition, and antioxidant activity of calabura (Muntingia calabura L.) fruit was written by Pereira, Gustavo Araujo;Arruda, Henrique Silvano;Rodrigues de Morais, Damila;Eberlin, Marcos Nogueira;Pastore, Glaucia Maria. And the article was included in Food Research International in 2018.Safety of (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol This article mentions the following:

Soluble carbohydrates, volatile and phenolic compounds from calabura fruit as well as its antioxidant activity were assessed. The low amount of fermentable oligo-, di-, and monosaccharides and polyols (FODMAPs) and similar amount of glucose and fructose allow us to classify the calabura berry as low-FODMAPs. The terpenes β-Farnesene and dendrolasin identified by SPME-GC-MS were the major volatile components. UHPLC-MS/MS anal. revelled gallic acid (5325 μg/g dw) and cyanidin-3-O-glucoside (171 μg/g dw) as the main phenolic compounds, followed by gentisic acid, gallocatechin, caffeic acid and protocatechuic acid. In addition, gallic acid was found mainly in esterified (2883 μg/g dw) and insoluble-bound (2272 μg/g dw) forms. Free and glycosylated forms showed however the highest antioxidant activity due to occurrence of flavonoids (0.28-27 μg/g dw) in these fractions, such as catechin, gallocatechin, epigallocatechin, naringenin, and quercetin. These findings clearly suggest that calabura is a berry with low energy value and attractive color and flavor that may contribute to the intake of several bioactive compounds with antioxidant activity. Furthermore, this berry have great potential for use in the food industry and as functional food. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9Safety of (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol).

(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Safety of (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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

Radical Carbonyl Umpolung Arylation via Dual Catalysis was written by Huang, Huan-Ming;Bellotti, Peter;Erchinger, Johannes E.;Paulisch, Tiffany O.;Glorius, Frank. And the article was included in Journal of the American Chemical Society in 2022.Recommanded Product: (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol This article mentions the following:

A series of aryl benzoates I [R = iPr, tBu, cyclohexyl, etc.; R¹ = 4-NCC₆H₄, 2-NCC₆H₄, 2-pyridyl, etc.] via dual nickel and photoredox catalyzed radical carbonyl umpolung arylation of aldehydes and aryl bromides was reported. This redox-neutral approach provided a complementary method to construct Grignard-type products from (hetero)aryl bromides and aliphatic aldehydes, without the need for prefunctionalization. Sequential activation, hydrogen atom transfer and halogen atom transfer process could directly converted aldehydes to the corresponding ketyl radicals, which further react with aryl-nickel intermediates in an overall polarity-reversal process. This radical strategy tolerated-among others-acidic functional groups, heteroaryl motifs and sterically hindered substrates and was applied in the late-stage modification of drugs and natural products. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Recommanded Product: (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives.Tetrahydrofuran has many industry uses as a solvent including in natural and synthetic resins, high polymers, fat oils, rubber, polymer. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Recommanded Product: (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

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

Enzymatic transesterification between sucrose octaacetate and ethyl oleate was written by Wu, Hongda;Zhang, Xianhua;Li, Junsheng;Yan, Liujuan. And the article was included in Shipin Gongye Keji in 2005.Name: (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate This article mentions the following:

Synthesis of sucrose esters containing acetyl and oleoyl groups was performed by transesterification of sucrose octaacetate with Et oleate using lipase as catalyst. A 95% Et oleate conversion was obtained with reactant ratio of 1:1 and reaction time 5 h. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (cas: 126-14-7Name: (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate).

(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (cas: 126-14-7) 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. 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.Name: (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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

Chiral methylbenzylammonium salts of aryldithiophosphonic acids containing glucofuranose, allofuranose, and galactopyranose diacetonide scaffolds was written by Nizamov, Ilyas S.;Shumatbaev, Georgiy G.;Nizamov, Ilnar D.;Nikitin, Yevgeniy N.;Belov, Timur G.;Shulaeva, Marina P.;Pozdeev, Oscar K.;Batyeva, Elvira S.;Cherkasov, Rafael A.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2021.Formula: C12H20O6 This article mentions the following:

New chiral methylbenzylammonium salts of aryldithiophosphonic acids containing glucofuranose, allofuranose, and galactopyranose diacetonide substituents were obtained using (S)-(-)-α-methylbenzylamine, (R)-(+)-α-methylbenzylamine, and (R,S)-(±)-α-methylbenzylamine. Salts obtained possess antimicrobial activity. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Formula: C12H20O6).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) 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. 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.Formula: C12H20O6

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

Electrochemical-Promoted Nickel-Catalyzed Oxidative Fluoroalkylation of Aryl Iodides was written by Zou, Zhenlei;Li, Heyin;Huang, Mengjun;Zhang, Weigang;Zhi, Sanjun;Wang, Yi;Pan, Yi. And the article was included in Organic Letters in 2021.Safety of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol This article mentions the following:

This work describes a general strategy for metal-catalyzed cross-coupling of fluoroalkyl radicals with aryl halides ArX (Ar = biphenyl-4-yl, benzothiophen-3-yl, benzodioxol-5-yl, etc.; X = Br, I) under electrochem. conditions. The contradiction between anodic oxidation of fluoroalkyl sulfinates NaSO₂CF₂H, NaSO₂CH₂F and cathodic reduction of low-valent nickel catalysts can be well addressed by paired electrolysis, allowing for direct introduction of fluorinated functionalities into aromatic systems. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Safety of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. 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.Safety of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

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

Effect of amorphization method on the physicochemical properties of amorphous sucrose was written by Morrow, Elizabeth A.;Terban, Maxwell W.;Thomas, Leonard C.;Gray, Danielle L.;Bowman, Michael J.;Billinge, Simon J. L.;Schmidt, Shelly J.. And the article was included in Journal of Food Engineering in 2019.Recommanded Product: (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol This article mentions the following:

Our objective was to characterize the physicochem. properties of amorphous sucrose prepared by freeze-drying (FreD), spray-drying (SprayD), ball milling (BallM), melt-quenching (MeltQ), and spin-melt-quenching (SpinMeltQ). SEM indicated that FreD, SprayD, BallM, and SpinMeltQ formed distinct particles, while MeltQ formed a single mass. Powder X-ray diffraction confirmed that BallM was semi-crystalline, while FreD, SprayD, MeltQ, and SpinMeltQ were amorphous. However, total scattering pair distribution function anal. of synchrotron X-ray diffraction data suggested that local mol.-level ordering differences existed between MeltQ and FreD, SprayD, and SpinMeltQ. Chromatog. analyses revealed that thermal decomposition indicator compounds were present in BallM, MeltQ, and SpinMeltQ, but not in FreD and SprayD. All samples exhibited a glass transition. Addnl., FreD, SprayD, BallM, and SpinMeltQ exhibited an exothermic cold crystallization peak, but MeltQ did not. Overall, this research provides evidence that sucrose is a material whose physicochem. properties are strongly influenced by amorphization method. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9Recommanded Product: (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol).

(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9) 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.Recommanded Product: (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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

Stereoselective Synthesis of 1,1′-Disaccharides by Organoboron Catalysis was written by Izumi, Sanae;Kobayashi, Yusuke;Takemoto, Yoshiji. And the article was included in Angewandte Chemie, International Edition in 2020.Electric Literature of C12H20O6 This article mentions the following:

The highly stereoselective synthesis of 1,1′-disaccharides was achieved by using 1,2-dihydroxyglycosyl acceptors and glycosyl donors in the presence of a tricyclic borinic acid catalyst. In this reaction, the complexation of the diols and the catalyst is crucial for the activation of glycosyl donors, as well as for the 1,2-cis-configuration of the products. The anomeric stereochem. of the glycosyl donor depends on the employed glycosyl donor. Applications of the produced 1,1′-disaccharides are also described. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Electric Literature of C12H20O6).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. 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.Electric Literature of C12H20O6

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

Opposite fates of the purine metabolite allantoin under water and nitrogen limitations in bread wheat was written by Casartelli, Alberto;Melino, Vanessa J.;Baumann, Ute;Riboni, Matteo;Suchecki, Radoslaw;Jayasinghe, Nirupama S.;Mendis, Himasha;Watanabe, Mutsumi;Erban, Alexander;Zuther, Ellen;Hoefgen, Rainer;Roessner, Ute;Okamoto, Mamoru;Heuer, Sigrid. And the article was included in Plant Molecular Biology in 2019.Formula: C18H32O16 This article mentions the following:

Abstract: The metabolite allantoin is an intermediate of the catabolism of purines (components of nucleotides) and is known for its housekeeping role in nitrogen (N) recycling and also for its function in N transport and storage in nodulated legumes. Allantoin was also shown to differentially accumulate upon abiotic stress in a range of plant species but little is known about its role in cereals. To address this, purine catabolic pathway genes were identified in hexaploid bread wheat and their chromosomal location was exptl. validated. A comparative study of two Australian bread wheat genotypes revealed a highly significant increase of allantoin (up to 29-fold) under drought. In contrast, allantoin significantly decreased (up to 22-fold) in response to N deficiency. The observed changes were accompanied by transcriptional adjustment of key purine catabolic genes, suggesting that the recycling of purine-derived N is tightly regulated under stress. We propose opposite fates of allantoin in plants under stress: the accumulation of allantoin under drought circumvents its degradation to ammonium (NH₄⁺) thereby preventing N losses. On the other hand, under N deficiency, increasing the NH₄⁺ liberated via allantoin catabolism contributes towards the maintenance of N homeostasis. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9Formula: C18H32O16).

(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9) 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. 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.Formula: C18H32O16

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

Conformational Lock of Glycosyl Donors Using Cyclic Carbamates was written by Villameriel, Jaime Moyano;Pedersen, Christian Marcus. And the article was included in European Journal of Organic Chemistry in 2020.Computed Properties of C12H20O6 This article mentions the following:

Axial rich glycosyl donors often display superior reactivity and stereoselectivity in glycosylation. In this study, a glucosamine glycosyl donor, locked in a ¹C₄ conformation by a six-membered carbamate ring, i.e. an oxazinone, is synthesized and studied. The 2N,4O carbamate is synthesized in one step from the corresponding azide. The glycosylation properties were studied by glycosylation of different alcs. Derivatives of the glycosyl donor were synthesized by introducing Ac, Troc, Ts, and Ms groups on the oxazinone nitrogen. The ring opening to give the glycoside in the ⁴C₁ conformation was found to proceed smoothly using Zemplen conditions. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Computed Properties of C12H20O6).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) 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. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Computed Properties of C12H20O6

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