Category: 4098-06-0

Qin, Chunjun; Liu, Zhonghua; Ding, Meiru; Cai, Juntao; Fu, Junjie; Hu, Jing; Seeberger, Peter H.; Yin, Jian published the artcile< Chemical synthesis of the Pseudomonas aeruginosa O11 O-antigen trisaccharide based on neighboring electron-donating effect>, SDS of cas: 4098-06-0, the main research area is glycosyl trifluoroacetimidate glycosylation galactose steric effect; Pseudomonas aeruginosa antigen trisaccharide neighboring electron donating synthesis fucosamine.

Pseudomonas aeruginosa O11 O-antigen is immunol. active but an exact protective epitope has not yet been identified. Synthesis of O11 O-antigen trisaccharide is of importance for identifying the epitopes. Here, neighboring electron-donating effects are keys to enhance the nucleophilicity of the C3 hydroxyl groups of D- and L-fucosamines, to facilitate the efficient synthesis of the trisaccharide. The disarmed peracetylated glycosyl donor with low glycosylation reactivity and glycosyl trifluoroacetimidate with good stability allowed for the glycosylation under mild conditions. The C6 nucleophilic tosylate substitution of D-galactose with iodine was found to be dependent on the steric effect of the axial C4.

Journal of Carbohydrate Chemistry published new progress about Antigens Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, SDS of cas: 4098-06-0.

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

Ding, Zekun; Luo, Xiaosheng; Ma, Yibin; Chen, Heshan; Qiu, Saifeng; Sun, Guosheng; Zhang, Wan; Yu, Chao; Wu, Zhenliang; Zhang, Jianbo published the artcile< Eco-friendly synthesis of 5-hydroxymethylfurfural (HMF) and its application to the Ferrier-rearrangement reaction>, SDS of cas: 4098-06-0, the main research area is hydroxymethylfurfural green synthesis; Ferrier rearrangement synthesis hydroxymethylfurfural unsaturated glycoside.

5-Hydroxymethylfurfural was conveniently synthesized by dehydration of D-fructose in a good yield. To further build bioactive derivatives from 5-hydroxymethylfurfural, 2,3-unsaturated glycosides were directly obtained through the Ferrier-rearrangement reaction of various glycals. Noticeably, a solid acid catalyst was successfully applied in the preparation of 5-hydroxymethylfurfural and then recycled to promote the Ferrier-rearrangement reaction, making it possible to achieve two steps of reaction in an eco-friendly manner through the simple process.

Journal of Carbohydrate Chemistry published new progress about Antitumor agents. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, SDS of cas: 4098-06-0.

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

Rasool, Faheem; Ahmed, Ajaz; Hussain, Nazar; Yousuf, Syed Khalid; Mukherjee, Debaraj published the artcile< One-Pot Regioselective and Stereoselective Synthesis of C-Glycosyl Amides from Glycals Using Vinyl Azides as Glycosyl Acceptors>, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is C glycosyl amide regioselective stereoselective synthesis glycal vinyl azide.

The reaction of glycals containing good leaving groups with aromatic vinyl azides to give α-C-glycosyl amides in good yields is described. Various vinyl azides with different groups undergo the reaction smoothly. In these reactions, an iminodiazonium intermediate is generated by the attack of the vinyl azide onto the glycal under Lewis acid conditions. This undergoes Schmidt-type denitrogenative 1,2-migration to form a nitrilium ion, which, upon hydrolysis, gives the desired C-glycosyl amide.

Organic Letters published new progress about Azides Role: RCT (Reactant), RACT (Reactant or Reagent) (aryl vinyl). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate.

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

Palo-Nieto, Carlos; Sau, Abhijit; Jeanneret, Robin; Payard, Pierre-Adrien; Salame, Aude; Martins-Teixeira, Maristela Braga; Carvalho, Ivone; Grimaud, Laurence; Galan, M. Carmen published the artcile< Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals>, Computed Properties of 4098-06-0, the main research area is glycal deoxy glycoside copper catalyst stereoselective glycosylation disaccharide.

We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both “”armed”” and “”disarmed”” type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxy-glycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

Organic Letters published new progress about Disaccharides Role: SPN (Synthetic Preparation), PREP (Preparation). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Computed Properties of 4098-06-0.

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

Chang, Chun-Wei; Wu, Chia-Hui; Lin, Mei-Huei; Liao, Pin-Hsuan; Chang, Chun-Chi; Chuang, Hsiao-Han; Lin, Su-Ching; Lam, Sarah; Verma, Ved Prakash; Hsu, Chao-Ping; Wang, Cheng-Chung published the artcile< Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity>, Reference of 4098-06-0, the main research area is predicted stereocontrolled glycosylation relative reactivity thioglycoside; carbohydrates; diastereoselectivity; glycosylation.

Stereocontrolled chem. glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

Angewandte Chemie, International Edition published new progress about Diastereoselective synthesis. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Reference of 4098-06-0.

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

Ahadi, Somayeh; Awan, Shahid I.; Werz, Daniel B. published the artcile< Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34>, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is synthon lipopolysaccharide Providencia rustigianii oligosaccharide preparation galactosamine coupling; oligosaccharide aminoglycoside preparation Providencia rustigianii polysaccharide coupling Birch; Providencia rustigianii; fucose; glycosylation; lipopolysaccharide (LPS); oligosaccharides.

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] coupling. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

Chemistry – A European Journal published new progress about Aminoglycosides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate.

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

Qin, Chunjun; Liu, Zhonghua; Ding, Meiru; Cai, Juntao; Fu, Junjie; Hu, Jing; Seeberger, Peter H.; Yin, Jian published the artcile< Chemical synthesis of the Pseudomonas aeruginosa O11 O-antigen trisaccharide based on neighboring electron-donating effect>, SDS of cas: 4098-06-0, the main research area is glycosyl trifluoroacetimidate glycosylation galactose steric effect; Pseudomonas aeruginosa antigen trisaccharide neighboring electron donating synthesis fucosamine.

Pseudomonas aeruginosa O11 O-antigen is immunol. active but an exact protective epitope has not yet been identified. Synthesis of O11 O-antigen trisaccharide is of importance for identifying the epitopes. Here, neighboring electron-donating effects are keys to enhance the nucleophilicity of the C3 hydroxyl groups of D- and L-fucosamines, to facilitate the efficient synthesis of the trisaccharide. The disarmed peracetylated glycosyl donor with low glycosylation reactivity and glycosyl trifluoroacetimidate with good stability allowed for the glycosylation under mild conditions. The C6 nucleophilic tosylate substitution of D-galactose with iodine was found to be dependent on the steric effect of the axial C4.

Journal of Carbohydrate Chemistry published new progress about Antigens Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, SDS of cas: 4098-06-0.

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

Ding, Zekun; Luo, Xiaosheng; Ma, Yibin; Chen, Heshan; Qiu, Saifeng; Sun, Guosheng; Zhang, Wan; Yu, Chao; Wu, Zhenliang; Zhang, Jianbo published the artcile< Eco-friendly synthesis of 5-hydroxymethylfurfural (HMF) and its application to the Ferrier-rearrangement reaction>, SDS of cas: 4098-06-0, the main research area is hydroxymethylfurfural green synthesis; Ferrier rearrangement synthesis hydroxymethylfurfural unsaturated glycoside.

5-Hydroxymethylfurfural was conveniently synthesized by dehydration of D-fructose in a good yield. To further build bioactive derivatives from 5-hydroxymethylfurfural, 2,3-unsaturated glycosides were directly obtained through the Ferrier-rearrangement reaction of various glycals. Noticeably, a solid acid catalyst was successfully applied in the preparation of 5-hydroxymethylfurfural and then recycled to promote the Ferrier-rearrangement reaction, making it possible to achieve two steps of reaction in an eco-friendly manner through the simple process.

Journal of Carbohydrate Chemistry published new progress about Antitumor agents. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, SDS of cas: 4098-06-0.

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

Ding, Zekun; Luo, Xiaosheng; Ma, Yibin; Chen, Heshan; Qiu, Saifeng; Sun, Guosheng; Zhang, Wan; Yu, Chao; Wu, Zhenliang; Zhang, Jianbo published the artcile< Eco-friendly synthesis of 5-hydroxymethylfurfural (HMF) and its application to the Ferrier-rearrangement reaction>, SDS of cas: 4098-06-0, the main research area is hydroxymethylfurfural green synthesis; Ferrier rearrangement synthesis hydroxymethylfurfural unsaturated glycoside.

5-Hydroxymethylfurfural was conveniently synthesized by dehydration of D-fructose in a good yield. To further build bioactive derivatives from 5-hydroxymethylfurfural, 2,3-unsaturated glycosides were directly obtained through the Ferrier-rearrangement reaction of various glycals. Noticeably, a solid acid catalyst was successfully applied in the preparation of 5-hydroxymethylfurfural and then recycled to promote the Ferrier-rearrangement reaction, making it possible to achieve two steps of reaction in an eco-friendly manner through the simple process.

Journal of Carbohydrate Chemistry published new progress about Antitumor agents. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, SDS of cas: 4098-06-0.

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

Denavit, Vincent; Laine, Danny; Bouzriba, Chahrazed; Shanina, Elena; Gillon, Emilie; Fortin, Sebastien; Rademacher, Christoph; Imberty, Anne; Giguere, Denis published the artcile< Stereoselective Synthesis of Fluorinated Galactopyranosides as Potential Molecular Probes for Galactophilic Proteins: Assessment of Monofluorogalactoside-LecA Interactions>, Name: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is stereoselective galactopyranoside galactophilic protein monofluorogalactoside LecA interaction; crystal structure; LecA; NMR spectroscopy; TROSY NMR; carbohydrates; fluorinated glycoside.

The replacement of hydroxyl groups by fluorine atoms on hexopyranoside scaffolds may allow access to invaluable tools for studying various biochem. processes. As part of ongoing activities toward the preparation of fluorinated carbohydrates, a systematic investigation involving the synthesis and biol. evaluation of a series of mono- and polyfluorinated galactopyranosides is described. Various monofluorogalactopyranosides, a trifluorinated, and a tetrafluorinated galactopyranoside have been prepared using a Chiron approach. Given the scarcity of these compounds in the literature, in addition to their synthesis, their biol. profiles were evaluated. Firstly, the fluorinated compounds were investigated as antiproliferative agents using normal human and mouse cells in comparison with cancerous cells. Most of the fluorinated compounds showed no antiproliferative activity. Secondly, these carbohydrate probes were used as potential inhibitors of galactophilic lectins. The first transverse relaxation-optimized spectroscopy (TROSY) NMR experiments were performed on these interactions, examining chem. shift perturbations of the backbone resonances of LecA, a virulence factor from Pseudomonas aeruginosa. Moreover, taking advantage of the fluorine atom, the 19F NMR resonances of the monofluorogalactopyranosides were directly monitored in the presence and absence of LecA to assess ligand binding. Lastly, these results were corroborated with the binding potencies of the monofluorinated galactopyranoside derivatives by isothermal titration calorimetry experiments Analogs with fluorine atoms at C-3 and C-4 showed weaker affinities with LecA as compared to those with the fluorine atom at C-2 or C-6. This research has focused on the chem. synthesis of “”drug-like”” low-mol.-weight inhibitors that circumvent drawbacks typically associated with natural oligosaccharides.

Chemistry – A European Journal published new progress about Antitumor agents. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Name: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate.

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