Category: 4098-06-0

Guberman, Monica; Pieber, Bartholomaeus; Seeberger, Peter H. published the artcile< Safe and Scalable Continuous Flow Azidophenylselenylation of Galactal to Prepare Galactosamine Building Blocks>, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is azidophenyl selenylation galactal galactosamine glycoside preparation.

Differentially protected galactosamine building blocks are key components for the synthesis of human and bacterial oligosaccharides. The azidophenylselenylation of 3,4,6-tri-O-acetyl-D-galactal provides straightforward access to the corresponding 2-nitrogenated glycoside. Poor reproducibility and the use of azides that lead to the formation of potentially explosive and toxic species limit the scalability of this reaction and render it a bottleneck for carbohydrate synthesis. Here, we present a method for the safe, efficient, and reliable azidophenylselenylation of 3,4,6-tri-O-acetyl-D-galactal at room temperature, using continuous flow chem. Careful anal. of the transformation resulted in reaction conditions that produce minimal side products while the reaction time was reduced drastically when compared to batch reactions. The flow setup is readily scalable to process 5 mmol of galactal in 3 h, producing 1.2 mmol/h of product.

Organic Process Research & Development published new progress about Glycosides 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

Lucchetti, Nicola; Gilmour, Ryan published the artcile< Reengineering Chemical Glycosylation: Direct, Metal-Free Anomeric O-Arylation of Unactivated Carbohydrates>, COA of Formula: C12H16O7, the main research area is aryl glycoside preparation anomeric arylation unactivated lactol diaryliodonium salt; acetals; arylation; carbohydrates; fluorine; stereoretention.

To sustain innovation in glycobiol., effective routes to well-defined carbohydrate probes must be developed. For over a century, glycosylation has been dominated by the formation of the anomeric Csp3-O acetal junction in glycostructures. A dissociative mechanistic spectrum spanning SN1 and SN2 is frequently operational thereby reducing the efficiency. By reengineering this fundamental process, an orthogonal disconnection allows the acetal to be formed directly from the reducing sugar without the need for substrate pre-functionalization. The use of stable aryliodonium salts facilitates a formal O-H functionalization reaction. This allows lactols to undergo mild, metal-free O-arylation at ambient temperature The efficiency of the transformation has been validated using a variety of pyranoside and furanoside monosaccharides in addition to biol. relevant di- and trisaccharides (up to 85 %). Fluorinated mechanistic probes that augment the anomeric effect were employed. It is envisaged that this strategy will prove expansive for the construction of complex acetals under substrate-based stereocontrol.

Chemistry – A European Journal published new progress about Anomeric effect. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, COA of Formula: C12H16O7.

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

Si, Anshupriya; Misra, Anup Kumar published the artcile< Facile synthesis of a rare sugar intermediate: D-gulopyranosyl cyanide>, Synthetic Route of 4098-06-0, the main research area is glycoside nitrile gulopyranosyl cyanide glycosylation preparation hydroxylation.

Convenient synthesis of D-gulopyranosyl cyanide has been achieved in high yield using a two step reaction sequence from D-galactal derivative The reaction condition is simple and suitable for scaling up. A bi-metallic reagent system consisting of CeCl3.7H2O and RuCl3.H2O has been used for the NaIO4 mediated cis-dihydroxylation of sugar olefin derivative i.e. pseudo-glycal.

Trends in Carbohydrate Research published new progress about Cyanation. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Synthetic Route of 4098-06-0.

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

Fomitskaya, Polina A.; Argunov, Dmitry A.; Tsvetkov, Yury E.; Lalov, Andrey V.; Ustyuzhanina, Nadezhda E.; Nifantiev, Nikolay E. published the artcile< Further Investigation of the 2-Azido-phenylselenylation of Glycals>, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is oligosaccharide aminodeoxy sugar azidodeoxy bacterial synthon stereoselective azidophenylselenylation glycal; crystal structure azidophenylselenylation glycal mannopyranoside azidodeoxyseleno glycoside preparation acetoxyphenylselenylation.

Derivatives of 2-azido-2-deoxy sugars are widely applied as precursor of 2-amino-2-deoxy sugars in the synthesis of various oligosaccharides of bacterial, fungal and mammalian origin. Heterogeneous or homogeneous azidophenylselenylation (APS) of glycals, i. e., reaction of glycals with Ph2Se2, PhI(OAc)2 and NaN3 or TMSN3 as azide radical donors, is a straightforward way to Ph 2-azido-2-deoxy-1-selenoglycosides that can be directly used as glycosyl donors. However, heterogeneous APS is characterized by insufficient reproducibility and scalability. We have studied the effect of reaction conditions on the product distribution in heterogeneous APS of 3,4,6-tri-O-acetyl-D-galactal and found the conditions that enabled reliable preparation of crystalline Ph 2-azido-2-deoxy-1-seleno-α-D-galactopyranoside triacetate in yield of 58% on the 3.7 mmol scale. APS of 3,4,6-tri-O-acetyl-D-glucal under those conditions produced a ∼1 : 1 mixture of Ph 2-azido-2-deoxy-1-seleno-α-D-gluco- and mannopyranosides in total yield of 78%. Acetoxyphenylselenylation of differently protected galactals and 3,4,6-tri-O-acetyl-D-glucal under the action of Ph2Se2 and PhI(OAc)2 has been shown to be a convenient method for the synthesis of 1-O-acetyl-2-seleno-2-deoxy derivatives, valuable intermediates in chem. of 2-deoxysugars. 2-Seleno-2-deoxy sugars were characterized in detail by NMR data including 77Se chem. shifts and nJSe-H coupling constant values.

European Journal of Organic Chemistry published new progress about Crystal structure. 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

Li, Jiagen; Wang, Ming; Jiang, Xuefeng published the artcile< Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement>, Formula: C12H16O7, the main research area is diosgenyl rhamnoside isoquercitrin rearrangement sulfoxide rhamnoside glucoside; stereoselective glycosylation thioglycosylation thioglycoside thiosulfate glycal; crystal structure stereoselective allylic rearrangement palladium catalyzed.

Stereoselective glycosylation is challenging in carbohydrate chem. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-L-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, resp.

Organic Letters published new progress about Crystal structure. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Formula: C12H16O7.

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

Greis, Kim; Kirschbaum, Carla; Leichnitz, Sabrina; Gewinner, Sandy; Schoellkopf, Wieland; von Helden, Gert; Meijer, Gerard; Seeberger, Peter H.; Pagel, Kevin published the artcile< Direct Experimental Characterization of the Ferrier Glycosyl Cation in the Gas Phase>, Formula: C12H16O7, the main research area is Ferrier glycosyl cation gas phase structure exptl characterization.

The Ferrier rearrangement reaction is crucial for the synthesis of pharmaceuticals. Although its mechanism was described more than 50 years ago, the structure of the intermediate remains elusive. Two structures have been proposed for this Ferrier glycosyl cation: a 1,2-unsaturated cation that is resonance-stabilized within the pyranose ring or a cation that is stabilized by the anchimeric assistance of a neighboring acetyl group. Using a combination of gas-phase cryogenic IR spectroscopy in helium nanodroplets and first-principles d. functional theory, we provide the first direct structural characterization of Ferrier cations. The data show that both acetylated glucal and galactal lead to glycosyl cations of the dioxolenium type.

Organic Letters published new progress about Conformation. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Formula: C12H16O7.

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

Lebedel, Ludivine; Arda, Ana; Martin, Amelie; Desire, Jerome; Mingot, Agnes; Aufiero, Marialuisa; Aiguabella Font, Nuria; Gilmour, Ryan; Jimenez-Barbero, Jesus; Bleriot, Yves; Thibaudeau, Sebastien published the artcile< Structural and Computational Analysis of 2-Halogeno-Glycosyl Cations in the Presence of a Superacid: An Expansive Platform>, Synthetic Route of 4098-06-0, the main research area is NMR DFT conformational analysis haloglycosyl cation superacid; conformation analysis; fluorine; glycosylation; reaction mechanisms; superacids.

An expansive NMR-based structural anal. of elusive glycosyl cations derived from natural and non-natural monosaccharides in superacids is disclosed. For the first time, it has been possible to explore the consequence of deoxygenation and halogen substitution at the C2 position in a series of 2-halogenoglucosyl, galactosyl, and mannosyl donors in the condensed phase. These cationic intermediates were characterized using low-temperature in situ NMR experiments supported by DFT calculations The 2-bromo derivatives display intramol. stabilization of the glycosyl cations. Introducing a strongly electron-withdrawing fluorine atom at C2 exerts considerable influence on the oxocarbenium ion reactivity. In a superacid, these oxocarbenium ions are quenched by weakly coordinating SbF6- anions, thereby demonstrating their highly electrophilic character and their propensity to interact with poor nucleophiles.

Angewandte Chemie, International Edition published new progress about Carbocations, carbenium (oxo). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Synthetic Route of 4098-06-0.

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

Singh, YashoNandini; Rodriguez Benavente, Maria C.; Al-Huniti, Mohammed H.; Beckwith, Donella; Ayyalasomayajula, Ramya; Patino, Eric; Miranda, William S.; Wade, Alex; Cudic, Mare published the artcile< Positional Scanning MUC1 Glycopeptide Library Reveals the Importance of PDTR Epitope Glycosylation for Lectin Binding>, Electric Literature of 4098-06-0, the main research area is MUC1 glycopeptide epitope combinatorial library lectin binding cancer glycosylation.

One of the main barriers to explaining the functional significance of glycan-based changes in cancer is the natural epitope heterogeneity found on the surface of cancer cells. To help address this knowledge gap, we focused on designing synthetic tools to explore the role of tumor-associated glycans of MUC1 in the formation of metastasis via association with lectins. In this study, we have synthesized for the first time a MUC1-derived positional scanning synthetic glycopeptide combinatorial library (PS-SGCL) that vary in number and location of cancer-associated Tn antigen using the “”tea bag”” approach. The determination of the isokinetic ratios necessary for the equimolar incorporation of (glyco)amino acids mixtures to resin-bound amino acid was determined, along with developing an efficient protocol for on resin deprotection of O-acetyl groups. Enzyme-linked lectin assay (ELLA) was used to screen PS-SGCL against two plant lectins, Glycine max soybean agglutinin (SBA) and Vicia villosa (VVA). Results revealed a carbohydrate d.-dependent affinity trend and site-specific glycosylation requirements for high affinity binding to these lectins. Hence, PS-SGCLs provide a platform to systematically elucidate MUC1-lectin binding specificities, which in long term may provide a rational design for novel inhibitors of MUC1-lectin interactions involved in tumor spread and glycopeptide-based cancer vaccines.

Journal of Organic Chemistry published new progress about Agglutinins Role: ARU (Analytical Role, Unclassified), BSU (Biological Study, Unclassified), ANST (Analytical Study), BIOL (Biological Study) (soybean). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Electric Literature of 4098-06-0.

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

Kumar, Manoj; Gurawa, Aakanksha; Kumar, Nitin; Kashyap, Sudhir published the artcile< Bismuth-Catalyzed Stereoselective 2-Deoxyglycosylation of Disarmed/Armed Glycal Donors>, Product Details of C12H16O7, the main research area is amino acid glycoside oligosaccharide preparation stereoselective glycosylation catalyst trifluoromethylation.

Bi(OTf)3 promoted direct and highly stereoselective glycosylation of “”disarmed”” and “”armed”” glycals to synthesize 2-deoxyglycosides has been reported. The tunable and solvent-controlled chemoselective activation of deactivated glycal donors distinguishing the competitive Ferrier and 1,2-addition pathways was discovered to improve substrate scope. The practical versatility of the method has been amply demonstrated with the oligosaccharide syntheses and 2-deoxyglycosylation of high-value natural products and drugs.

Organic Letters published new progress about Amino acids 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, Product Details of C12H16O7.

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

Dash, Ashutosh K.; Madhubabu, Tatina; Yousuf, Syed Khalid; Raina, Sushil; Mukherjee, Debaraj published the artcile< One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals: Application in the synthesis of chromanone 3-C-glycosides>, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is Ferrier rearrangement glycal glycoside preparation Lewis catalyst stereoselective glycosylation; 2,3-Unsaturated glycosides; Acetophenones; Carbon-Ferrier rearrangement; Chromanone 3-C-glycosides; Glycopyranosides; Lewis acid.

One-pot carbon-Ferrier rearrangement of glycals with un-activated aryl Me ketones has been developed under mild Silyl triflate catalysis. Keto Me group of various aryl Me ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto functionalized C-glycosides in moderate to good yields with high æµ?selectivity. The versatility of this method has been extended to the synthesis of a small library of chromanone 3-C-glycosides.

Carbohydrate Research published new progress about C-Glycosides 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