117841-70-0

Upstream product

• 120316-59-8 C₆₁H₆₄O₁₀Se 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 160549-11-1 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 
• 532959-22-1 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid 
• 163916-60-7 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride 
• 91780-43-7 phenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-arabino-hexopyranoside 
• 1588522-52-4 C₂₈H₃₁O₆^(1-)*K⁽¹⁺⁾ 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1079205-73-4 C₃₇H₅₂O₆Si 
• 2873-29-2 D-glucal triacetate 
• 1360560-44-6 p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 125085-08-7 methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

Relevant academic research and scientific papers

Cyclopropenium cation promoted dehydrative glycosylations using 2-deoxy- and 2,6-dideoxy-sugar donors

Dehydrative glycosylation reactions using 2-deoxy- and 2,6-dideoxy-sugar donors promoted by a combination of 3,3-dichloro-1,2-diphenylcyclopropene and tetrabutylammonium iodide (TBAI) are described. The reactions are α-selective and proceed under mild con

Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals

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 deoxyglycosides 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.

Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides

The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodo

Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.

Environmentally benign and stereoselective construction of 2-deoxy and 2,6-dideoxy-β-glycosidic linkages employing 2-deoxy and 2,6-dideoxyglycosyl phosphites and montmorillonite K-10

The β-stereoselective glycosidations of 2-deoxy- and 2,6-dideoxyglycosyl diethyl phosphites with alcohols using a heterogeneous and environmentally benign solid acid, montmorillonite K-10, have been developed.

Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst

B(C6F5)3 enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α-O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile acceptor. The method is exemplified with the synthesis of a series of rare and biologically relevant glycoside analogues.

Reactions of Nucleophiles with Reactive Intermediates in the 3,4,6-Tri-O-benzyl-D-glucal-TfOH-n-Bu4NI Reaction System

The unique reactive intermediate formed in the 3,4,6-tri-O-benzyl-D-glucal- TfOH (triflic acid)-n-Bu4NI reaction system (in dichloromethane) reacted with nucleophiles in a regio- and stereoselective manner. These selectivities resulted in hithe

Polymer-supported selenium reagents for organic synthesis

Organoselenium resins 1-4 were prepared from polystyrene via lithiation and quenching with MeSeSeMe, and shown to react with a variety of substrates, aiding in useful functionalizations.

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.