Category: 604-69-3

Total synthesis of ceramides and β-O-glucosylceramides via intramolecular fatty acyl group migration was written by Gorantla, Jaggaiah N.;Santhi, Maniganda;Hua, Yanling;Ketudat Cairns, James R.. And the article was included in New Journal of Chemistry in 2022.SDS of cas: 604-69-3 The following contents are mentioned in the article:

Acyl migration of alkyl and aromatic acyl groups from an alc. to another alc. or amine is a phenomenon that occurs in nature and can be a bane to some synthetic strategies. An acyl migration-dependent method was developed for the synthesis of ceramide and glucosyl ceramide derivatives, in which the desired fatty acyl moiety acts both as protecting and migrating group. Removal of the tetrachlorophthalimido (TCP) group with ethylenediamine as a mild base at room temperature resulted in subsequent intramol. fatty acyl group migration from -O to -N, on sphingosine or peracetylated glucosyl sphingosine to yield the desired N-acylated products. A deacetylation reaction afforded the desired β-O-glucosylceramide derivatives I (R = C₁₅H₃₁, C₁₇H₃₅). Thus, the choice of the appropriate blocking group turns acyl migration into a tool for synthesis, rather than an impediment. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3SDS of cas: 604-69-3).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.SDS of cas: 604-69-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II was written by Hou, Zhuang;Li, Chuanchao;Liu, Yichuang;Zhang, Miao;Wang, Yitong;Fan, Zhanfang;Guo, Chun;Lin, Bin;Liu, Yang. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2020.Category: esters-buliding-blocks The following contents are mentioned in the article:

A series of new carbohydrate-based sulfonamide derivatives were designed, synthesized by employing the so-call ‘sugar-tail’ approach. The compounds were evaluated in vitro against a panel of CAs. Compared to their parent compound p-sulfamoylbenzoic acid, these compounds showed nearly 100-fold improvement in their binding affinities against hCA II in vitro. All of compounds showed great water solubility and the pH value of their water solutions of compounds is 7.0. Such properties are advantageous to make them much less irritating to the eye when applied topical glaucomatous drugs, compared to the relatively highly acidic dorzolamide preparations (pH 5.5). Notably, compounds , , demonstrated to topically lower intraocular pressure (IOP) in glaucomatous animals better than brinzolamide when applied as a 1% solution directly into the eye. Low cytotoxicity on human cornea epithelial cell was observed in the tested concentrations by the MTT assay. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Category: esters-buliding-blocks).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Streamlined Iterative Assembly of Thio-Oligosaccharides by Aqueous S-Glycosylation of Diverse Deoxythio Sugars was written by Wen, Peng;Jia, Peijing;Fan, Qiuhua;McCarty, Bethany J.;Tang, Weiping. And the article was included in ChemSusChem in 2022.Application of 604-69-3 The following contents are mentioned in the article:

A streamlined iterative assembly of thio-oligosaccharides was developed by aqueous glycosylation. Facile syntheses of various deoxythio sugars with the sulfur on different positions from com. available starting materials were described. These syntheses featured efficient chem. methods including our recently reported BTM-catalyzed site-selective acylation. The resulting deoxythio sugars could then be used for the Ca(OH)₂-promoted protecting group-free S-glycosylation in water at room temperature The aqueous glycosylation reaction proceeded smoothly to afford the corresponding 1,2-trans S-glycosides in good yields with high chemo- and stereoselectivity. An appropriate choice of protecting groups for the thiol in the glycosyl donor was necessary for the development of iterative synthesis of thio-oligosaccharides. The aqueous glycosylation was then applied to the synthesis of a trimannoside moiety of N-linked glycans core region. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Application of 604-69-3).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Application of 604-69-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Novel carbohydrate modified berberine derivatives: synthesis and in vitro anti-diabetic investigation was written by Han, Liwen;Sheng, Wenlong;Li, Xiaobin;Sik, Attila;Lin, Houwen;Liu, Kechun;Wang, Lizhen. And the article was included in MedChemComm in 2019.Related Products of 604-69-3 The following contents are mentioned in the article:

Berberine is a bioactive alkaloid used in Chinese medicine and has numerous pos. effects on biol. systems. This paper describes the facile and highly efficient synthesis of some carbohydrate modified berberine derivatives, and conjugation of the carbohydrate moiety with berberine was finished by “click” chem. The cytotoxicity and anti-diabetic measurements of all berberine derivatives were accomplished on HepG2 cell lines, and the results indicated that most of the derivatives exhibit higher anti-diabetic activity than berberine. The mannose modified berberine derivative has significantly lower cytotoxicity than berberine, and the induced IC50 value of this derivative is nearly 1.5 times that of berberine. Furthermore, this mannose modified berberine derivative exhibits high anti-diabetic activity at both high and low drug concentrations, thereby indicating its potential application for the development of novel anti-diabetic drugs. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Related Products of 604-69-3).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Related Products of 604-69-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Phenyl glycosides – Solid-state NMR, X-ray diffraction and conformational analysis using genetic algorithm was written by Walejko, Piotr;Bukowicki, Jaroslaw;Dobrzycki, Lukasz;Socha, Pawel;Paradowska, Katarzyna. And the article was included in Chemical Physics in 2019.Name: (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate The following contents are mentioned in the article:

The X-ray structures of 2,6-dimethylphenyl and Ph 2,3,4,6-tetra-O-acetyl β-glucosides and Ph α-mannoside were obtained. The independent part of the unit cell of the glycosides was formed by one mol., and for another glucoside, two mols. in the crystal cell were observed In deacetylated glycosides the crystal structure was established by a hydrogen bond network formed between the sugar hydroxyls and solvent mols. The ¹³C CPMAS NMR spectra of aryl glycosides were analyzed. In the spectrum of Ph peracetylated glucoside, doubling of the C4 aryl signal was observed which confirmed the presence of two independent mols. in the solid sample. The GAAGS (Genetic Algorithm-Assisted Grid Search) method was used to determine the low-energy conformers of α-mannosides and β-glucosides. The orientation of the aryl pendant group was calculated using Mol. Mechanics (MMFF94) as well as Quantum Mechanics theory (DFT, B3LYP/6-31 + G(d,p)). This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Name: (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Name: (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis and characterization of a small library of bis-glucosides: Influence of the nature of the diol/diphenol used in O-glucosylation was written by Patry, Stephane;Robitzer, Mike;Habas, Jean-Pierre. And the article was included in Carbohydrate Research in 2021.Electric Literature of C16H22O11 The following contents are mentioned in the article:

In this paper, the synthesis of different bisglucosides is investigated through the reaction of two acetylated glucose units with a diol (or diphenol) in order to develop a versatile mol. platform for the future development of bio-based polymers. A panel of five diols and one diphenol is initially used in order to examine the influence of their chem. skeleton on the reaction yield and both nature and proportion of formed species. Reaction products are identified using ¹H and ¹³C NMR spectroscopies completed by MALDI-TOF MS technique. The nucleophilicity of these dihydroxy compounds is identified as being the main factor that governs the reaction characteristics. In particular, the best selectivity is obtained with the use of hydroquinone. Inversely, byproducts (oligomers, deacetylated compounds) are observed with the diols defined by higher nucleophilicity despite the choice of stereoselective pathway using acyl protecting groups. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Electric Literature of C16H22O11).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Electric Literature of C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent was written by Kobayashi, Shoji;Tamura, Tomoki;Yoshimoto, Saki;Kawakami, Takashi;Masuyama, Araki. And the article was included in Chemistry – An Asian Journal in 2019.Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate The following contents are mentioned in the article:

For the first time, a comprehensive study on the performance of 4-methyltetrahydropyran (4-MeTHP) as an organic reaction solvent was reported. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen-metal exchange, reduction, oxidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This application suggests that 4-MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However, 4-MeTHP was found incompatible with strong Lewis acids, and the C-O bond was readily cleaved by treatment with BBr₃. Moreover, the radical-based degradation pathways of 4-MeTHP, THP and 2-MeTHF were elucidated on the basis of GC-MS analyses. The data reported herein is anticipated to be useful for a broad range of synthetic chemists, especially industrial process chemists, when selecting the reaction solvent with green chem. perspectives. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction was written by Zhou, Zhonggao;Xie, Qian;Li, Jing;Yuan, Yangyang;Liu, Yong;Liu, Yulong;Lu, Dongliang;Xie, Yongrong. And the article was included in Catalysis Letters in 2022.SDS of cas: 604-69-3 The following contents are mentioned in the article:

The first system controlled anomeric isomerism of glucopyranoside-functionalized N-heterocyclic carbenes based pyridine enhanced precatalyst preparation, stabilization and initiation type palladium(II) complexes (Glu-NHCs-Pd(II)-PEPPSI) were prepared and fully characterized. It is interesting to note that pure β-anomer PEPPSI complex was obtained, in which the Glu-substituent connects to the imidazole heterocycle ring N through ethoxy bridged anomeric carbon. In addition, the catalytic activities revealed that Glu-NHCs-Pd(II)-PEPPSI complexes are efficient catalysts for the aqueous Suzuki reaction. Under optimized conditions, a series of fluorene-cored functional materials with different aryl-substituents were synthesized through the Suzuki reaction with excellent yields. The Glu-NHCs-Pd(II)-PEPPSI complex containing bulky and rigid 2,5-dimethylphenyl group played an important role in maintaining the β conformation and improving the catalytic activity significantly. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3SDS of cas: 604-69-3).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.SDS of cas: 604-69-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Glycosylation of Tetrabromobisphenol A in Pumpkin was written by Hou, Xingwang;Yu, Miao;Liu, Aifeng;Wang, Xiaoyun;Li, Yanlin;Liu, Jiyan;Schnoor, Jerald L.;Jiang, Guibin. And the article was included in Environmental Science & Technology in 2019.Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate The following contents are mentioned in the article:

Tetrabromobisphenol A (TBBPA) is the most widely used brominated flame retardant (BFR), and it bioaccumulates throughout the food chains. Its fate in the first trophic level, plants, is of special interest. In this study, a four-day hydroponic exposure of TBBPA at a concentration of 1μmol L^-1 to pumpkin seedlings was conducted. A nontarget screening method for hydrophilic bromine-containing metabolites was modified, based on both typical isotope patterns of bromine and mass defect, and used to process mass spectra data. A total of 20 glycosylation and malonyl glycosylation metabolites were found for TBBPA in the pumpkin plants. Representative glycosyl TBBPA reference standards were synthesized to evaluate the contribution of this glycosylation process. Approx. 86% of parent TBBPA was metabolized to form those 20 glycosyl TBBPAs, showing that glycosylation was the most dominant metabolism pathway for TBBPA in pumpkin at the tested exposure concentration This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Quality Control of (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Total Synthesis of Pyrolaside B: Phenol Trimerization through Sequenced Oxidative C-C and C-O Coupling was written by Neuhaus, William C.;Kozlowski, Marisa C.. And the article was included in Angewandte Chemie, International Edition in 2020.Recommanded Product: 604-69-3 The following contents are mentioned in the article:

A facile method to oxidatively trimerize phenols using a catalytic aerobic copper system is described. The mechanism of this transformation was probed, yielding insight that enabled cross-coupling trimerizations. With this method, the natural product pyrolaside B (I) was synthesized for the first time. The key strategy used for this novel synthesis is the facile one-step construction of a spiroketal trimer intermediate II, which can be selectively reduced to give the natural product framework without recourse to stepwise Ullmann- and Suzuki-type couplings. As a result, pyrolaside B can be obtained expeditiously in five steps and 16% overall yield. Three other analogs were synthesized, thus highlighting the utility of the method, which provides new accessibility to this area of chem. space. A novel xanthene, III, was also synthesized through controlled Lewis acid promoted rearrangement of a spiroketal trimer. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Recommanded Product: 604-69-3).

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Recommanded Product: 604-69-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics