Diastereoselective Synthesis of Elongated Carbohydrate Analogues via the Indium Mediated Allylation of Disaccharides

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1st EuroCarb Young Researcher (ECYR) Workshop

CarboMet Workshop

Mini symposium: Glycobiology at the LUMC and beyond

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Diastereoselective Synthesis of Elongated Carbohydrate Analogues via the Indium Mediated Allylation of Disaccharides

Christian Denner 1 , Walther Schmid 1

1 University Of Vienna, Vienna, Austria

In Glycosciences the demand for efficient synthetic approaches towards complex carbohydrate structures is an important, still continuously growing research aim, because the isolation of complex natural glycans is not efficient in order to obtain quantitative amounts in high purity. Additionally, unnatural derivatives are often interesting variants for biomedical as well as medicinal applications. [1,2] In this context, the development of diastereoselective and efficient synthetic routes to elongated carbohydrates and oligosaccharides has been in our focus to contribute to this field. Therefore, we became interested in the indium-mediated allylation reaction for the elongation of carbohydrate moieties.[3,4] With the use of this reaction followed by ozonolysis, applied on disaccharides, various elongated carbohydrate analogs could be synthesized in a short, diastereoselective and efficient approach. This method has been applied to cellobiose, melibiose, lactose and maltose as starting materials. Results and experimental details will be presented.

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W. Binder, R. Prenner, W. Schmid, Tetrahedron 1994, 50, 749–758.

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