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

Session: 
PS2 Poster session 2 Even numbers
Code: 
P48
Location (hall): 
Foyer
Start/end time: 
Tuesday, July 2, 2019 - 15:45 to 17:15
Christian
Denner

Christian Denner1, Walther Schmid1

1University 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.

References: 
  1. P. Sears, C. Wong, Angew. Chemie - Int. Ed. 1999, 38, 2300–2324.
  2. S. Nishat, P. Andreana, Vaccines 2016, 4, 19.
  3. W. Schmid, G. M. Whitesides, J. Am. Chem. Soc. 1991, 113, 6674–6675.
  4. W. Binder, R. Prenner, W. Schmid, Tetrahedron 1994, 50, 749–758.

Sponsors

Sponsors