Orthogonal Sets of Protecting Groups in Saccharide Synthesis

Christian Vogel

University of Rostock, Department of Chemistry/Organic Chemistry,

Albert-Einstein-Str. 3a, D-18059 Rostock, Germany

Email: christian.vogel@chemie.uni-rostock.de

Content

1.         Modification of monosaccharides

1.1       Synthesis of L-fucose and L-fucose derivatives starting from D-galactose

1.2       Synthesis of D-galacturonates from D-galactose and their derivatization

1.3       Synthesis of D-galacturonate C-glycosides

2.         Oligosaccharide synthesis

2.1       Synthesis of glycosyl donors and acceptors of L-rhamnose

2.2       Synthesis of glycosyl donors and acceptors of D-galacturonate

2.3       The behaviour of several protecting groups in the course of glycosylation reaction

2.4       Stepwise and blockwise synthesis of oligosacchrides as well as polysaccharide synthesis

Abstract:

In the course of the lecture several strategies for the synthesis of complex mono-, oligo-, and polysaccharides will be discussed encompassing such issues as glycosyl donor and acceptor synthesis, glycosylation reaction, stereochemistry, and functional group interconversion. But, the basis of a synthetic plan to a complex natural product is formed by an intelligent concept of the protection/deprotection methodology. Therefore, the lecture will be foccussed on the relation­ship between the problem of functional group incompatibility in the synthesis of complex organic structures and the application of protecting groups into orthogonal sets.