Tetrasaccharide cap present in lipophosphoglycan of the Leishmania donovani responsible for visceral Leishmaniaisis is synthesized as a fully protected propargyl glycoside. AuBr(3) mediated selective glycosylation of propargyl 1,2-orthoester in the presence of propargyl glycoside is employed as a key step to obtain propargyl containing oligomers. Further, propargyl tetrasaccharide is connected with a long chain hydrocarbon containing azidothiol functionality situated at two terminal ends via 'click' reaction.
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AuBr(3) mediated glycosidations: synthesis of tetrasaccharide motif of the Leishmania donovani lipophosphoglycan.
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Department of Chemistry, Indian Insititute of Science Education & Research, Pune, 411 008, India.
Tetrasaccharide cap present in lipophosphoglycan of the Leishmania donovani responsible for visceral Leishmaniaisis is synthesized as a fully protected propargyl glycoside. AuBr(3) mediated selective glycosylation of propargyl 1,2-orthoester in the presence of propargyl glycoside is employed as a key step to obtain propargyl containing oligomers. Further, propargyl tetrasaccharide is connected with a long chain hydrocarbon containing azidothiol functionality situated at two terminal ends via 'click' reaction.
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Article Synopsis
- Scientists looked at how to activate a special chemical group called propargyloxy in a type of molecule called 1,2-orthoesters.
- They used a tiny bit of a substance called AuBr3 to help create new sugar molecules called disaccharides with a propargyl group at one end.
- Also, another type of molecule called propargyl ethers did not change during this process.
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