In orthogonal glycosidation a range of glycosyl donors that bear different leaving groups (LG₁/ LG₂) and that can be selectively activated in the presence of each other, are utilized. A highly reactive donor is required for the first glycosidation in the orthogonal sequence¹.

The O-glycosyl-N-methyl thiocarbamates (A), readily obtained from anomerically-unprotected sugars², are very reactive glycosyl donors. Thiocarbamates can be easily activated with bromine. On the other hand the S-ethyl glycosides (B), obtained from S-glycosyl-N-methyl thiocarbamates, can be used as glycosyl acceptors in the first step of orthogonal glycosylation sequence. The second step requires activation of disaccharide baring thioethyl group. This activation can be done with thiophilic reagents, thus with the addition of the second glycosyl acceptor (C) the orthogonal sequence can be completed. We will present the application of this method in the synthesis of trisaccharides. This methodology will be used in the preparation of biologically active glycoconjugates.

Acknowledgement

Research studies part-financed by the European Regional Development Fund (POIG. 01.01.02-14-102/09)

References

¹ J. Pietruszka in Carbohydrates (H.M.L. Osborn Ed.) Academic Press, 2003, 219-239.

² Barili P.L., Catelani G., D’Andrea F., De Rensis F., Falcini P. Carbohydrate Res. 1997, 298, 75-84; Ott A.J., Brackhagen M., Davtyan A., Nolting B., Boye H., Schoknecht A. and Vogel Ch. J. Carbohydrate Chemistry, 2001, 20, 611-636; Abbas S.A., Barlow J.J. and Matta K.L. Carbohydrate Res. 1981, 88, 51-60, Kasprzycka A., Ślusarczyk A. and Szeja W. Polish J. Chem. 2001, 75, 1303-1308; Kasprzycka A. and Szeja W. Polish J. Chem. 2005, 79, 329-333.

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