671809-99-7

Upstream product

• 502692-41-3 p-tolyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 

Downstream Products

• 1380218-36-9 C₃₄H₄₂ClN₃O₆ 
• 1380218-28-9 6-chlorohexyl 2-azido-3,4-di-O-benzyl-2-deoxy-1-α-D-glucopyranoside 
• 1380218-35-8 C₃₅H₃₇N₃O₅S 
• 1380218-20-1 p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside 

Relevant academic research and scientific papers

Efficient Strategy for α-Selective Glycosidation of d -Glucosamine and Its Application to the Synthesis of a Bacterial Capsular Polysaccharide Repeating Unit Containing Multiple α-Linked GlcNAc Residues

An efficient α-selective glycosylation method was developed for the synthesis of 2-deoxy-2-amino-d-glucosides based on synergetic α-directing effects of the TolSCl/AgOTf promotion system and the functional groups at the corresponding azido donor 6-O-position to exert steric β-shielding effect or remote participation in the glycosylation reaction. Its practicability was verified with a wide range of monosaccharide glycosyl acceptors and the first, one-pot synthesis of the challenging pentasaccharide repeating unit of an Acinetobacter baumannii K47 capsular polysaccharide.

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.

Application of 2-azido-2-deoxythioglycosides for β-glycoside formation and oligosaccharide synthesis

Most natural 2-acetamido-2-deoxyglycosides exist in a 1,2-trans-β- glycosidic configuration. This study investigated the use of 2-azido-2-deoxythioglycosides for 1,2-trans-β-glycosidic bond formation under low-concentration glycosylation conditions. Furth