Day: September 16, 2022

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

Zhou, Zheng Hong;Chen, Ru Yu published 《1,2-cyclic monoacyl-rac-glycerothio-phosphates of cantharidin analogs》. The research results were published in《Chinese Chemical Letters》 in 1999.Recommanded Product: 14166-28-0 The article conveys some information:

A series of diastereomeric 1,2-cyclic-3-acylglycerothiophosphates I [R = R¹ = H, R² = CO(CH₂)₁₆CH₃, X = O, CH₂; RR = bond, R¹ = H, R² = CO(CH₂)₁₆CH₃, X = O, CH₂; R = H, R¹ = Me, R² = CO(CH₂)₁₆CH₃, X = O] were synthesized starting from cantharidin II (R = H, R¹ = Me, X = O) and its analogs II (R = R¹ = H, X = O, CH₂; RR = bond, R¹ = H, X = O, CH₂) in a one-pot procedure in overall yields in the range of 44-55.5% by means of hexaethylphosphorus triamide as phosphorylating reagent. E.g., cantharidin was reacted with 2-aminoethanol to form the tricyclic imide, which underwent sequentially phosphorylation with P(NEt₂)₃ and iodine in benzene, esterification with glycerol 1-stearate, and sulfuration with S₈ to form both cis- and trans-I [R = H, R¹ = Me, R² = CO(CH₂)₁₆CH₃, X = O] with overall yield of 55.5%.(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.Recommanded Product: 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

Recommanded Product: (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione《Synthesis and characterization of novel hydrogenated poly(norbornene bisimide)s prepared from ring opening metathesis polymerization》 was published in 2011. The authors were Yoon, Kyung-Hwan;Park, Seung Beom;Park, Insook;Yoon, Do Y., and the article was included in《Bulletin of the Korean Chemical Society》. The author mentioned the following in the article:

We synthesized three novel poly(norbornene bisimide)s by ring opening metathesis polymerization (ROMP) and subsequent hydrogenation. Their thermal, mech. and optical properties were investigated with TGA, DMA, UV-Vis spectrometer, and optical reflectometer. The new polymers showed high glass transition temperatures over 260° and good thermal stability with 5% wt-loss temperature higher than 390°. When solvent casted, they yielded optically transparent and dimensionally stable films with a relatively low coefficient of thermal expansion of about 50 ppm K^-1. Therefore, the bisimide moieties substantially enhanced thermal and dimensional stabilities, as compared with normal ROMP-prepared polynorbornene films. Though the water uptake was increased to 0.6%, this water uptake is still considerably lower than that for polyethersulfones (1.4%) or polyimides (2.0 wt-%). Hence, the new poly(norbornene bisimide)s may become attractive candidates for flexible substrates of optoelectronic devices such as displays and photovoltaic solar cells. And (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) was used in the research process.

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.Recommanded Product: (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

Shi, Zhen-Dan;Yang, Bing-Hui;Wu, Yu-Lin published 《A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides》 in 2002. The article was appeared in 《Tetrahedron》. They have made some progress in their research.Name: (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate The article mentions the following:

Using an inexpensive D-galactose from the chiral pool, L-deoxyribose, L-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis of L-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-L-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis of L-ribose, the key step of inversion of the 2-hydroxy group in the same substrate was carried out by intramol. S_N2 tandem reaction. Then the L-ribosyl donors were submitted to glycosidations according to Vorbruggen’s conditions to give L-ribosides (L-uridine, L-5-fluorouridine, L-iodouridine, L-thymidine, L-puridine, L-adenosine and L-guanosine) in excellent yields.(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 Name: (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

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

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

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

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

Safety of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateIn 2020, Wu, Ming-hao;Ai, Su;Chen, Qing;Chen, Xiang-yan;Li, Hong-jin;Li, Yu-lei;Zhao, Xia published 《Effects of Glycosylation and D-Amino Acid Substitution on the Antitumor and Antibacterial Activities of Bee Venom Peptide HYL》. 《Bioconjugate Chemistry》published the findings. The article contains the following contents:

Glycosylation is a promising strategy for modulating the physicochem. properties of peptides. However, the influence of glycosylation on the biol. activities of peptides remains unknown. Here, we chose the bee venom peptide HYL as a model peptide and 12 different monosaccharides as model sugars to study the effects of glycosylation site, number, and monosaccharide structure on the biochem. properties, activities, and cellular selectivities of HYL derivatives Some analogs of HYL showed improvement not only in cell selectivity and proteolytic stability but also in antitumor and antimicrobial activity. Moreover, we found that the helicity of glycopeptides can affect its antitumor activity and proteolytic stability, and the α-linked D-monosaccharides can effectively improve the antitumor activity of HYL. Therefore, it is possible to design peptides with improved properties by varying the number, structure, and position of monosaccharides. What’s more, the glycopeptides HYL-31 and HYL-33 show a promising prospect for antitumor and antimicrobial drugs development, resp. In addition, we found that the D-lysine substitution strategy can significantly improve the proteolytic stability of HYL. Our new approach provides a reference or guidance for the research of novel antitumor and antimicrobial peptide drugs. 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 Safety 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