Abstract
The novel sialyl donor methyl (ethyl 4,7,8,9-tetra- O-acetyl-5- N, N-diacetylamino-3,5-dideoxy-2-thio-3-thiophenyl- d- erythro-β- l- gluco-non-2-ulopyranosid)onate was used for glycosylation of a lactosyl acceptor to give the GM3-trisaccharide derivative in 83% yield. Introduction of an azido group at C-9′′ of the GM3-trisaccharide derivative, transformation into a glycosyl acceptor, and sialylation with the above mentioned novel sialyl donor gave a GD3-trisaccharide in 50% yield. Reduction of the azido group gave the corresponding amine, which underwent spontaneous lactamization to the GD3-[1′′′–9′′]-lactam in an overall yield of 86%. Removal of protecting groups of over five steps, followed by per- O-acetylation gave an acetylated GD3-[1′′′–9′′]-lactam TMSEt glycoside in 27% overall yield. The acetylated GD3-[1′′′–9′′]-lactam TMSEt glycoside is suitable for glycosylation of linker-arms and the resulting linker-glycosides are planned to be coupled to carrier proteins, thus providing immunogens for trial vaccinations against malignant melanoma.
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