762287-73-0

Upstream product

• 139903-49-4 phenyl 2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glycopyranoside 
• 479252-05-6 ((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 132201-75-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 850416-39-6 p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 762287-68-3 p-tolyl-2,3,4-tri-O-benzyl-6-O-trityl-1-thio-β-D-glucopyranoside 
• 819814-42-1 β-1-p-tolylthio-6-O-trityl-D-glucopyranose 
• 106-45-6 para-thiocresol 
• 83-87-4 D-glucose pentaacetate 

Relevant academic research and scientific papers

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.

Pre-activation based stereoselective glycosylations: Stereochemical control by additives and solvent

Stereochemical control is an important issue in carbohydrate synthesis. Glycosyl donors with participating acyl protective groups on 2-O have been shown to give 1,2-trans glycosides reliably under the pre-activation based reaction condition. In this work,

Solvent participation in a one-pot glycosylation strategy (SPOG)

Solvent participation in a one-pot glycosylation strategy (SPOG) was developed on the basis of the low concentration β-selective glycosylation method. This strategy enables the production of a β-glycosidic bond in a one-pot oligosaccharide synthesis without or with minimal use of any C-2 participating function.

Selective electrochemical glycosylation by reactivity tuning

Electrochemical glycosylation of a selenoglycoside donor proceeds efficiently in an undivided cell in acetonitrile to yield β-glycosides. Measurement of cyclic voltammograms for a selection of seleno-, thio-, and O-glycosides indicates the dependence of o