K. Jensen, M. Meldal, K. Bock
1993
Citations
0
Influential Citations
42
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
The synthesis of four building blocks, Nα-Fmoc-Tyr(Ac4-β-D-Glc)-OPfp 6, Nα- Fmoc-Tyr(Bz4-α-D-Glc)-OPfp 16, Nα-Fmoc-Tyr[Ac3-α-D-Glc]-(1→4)-Ac3-[β-D-Glc]-OPfp 9 and Nα-Fmoc-Tyr[Bz4-α-D-Glc-(1 →4)-Bz3-α-D-Glc]-OPfp 19, suitable for solid-phase glycopeptide synthesis is described. Several different glycosylation procedures were evaluated for this purpose. A remarkable solvent effect on the α:β ratio was observed on going from dichloromethane to the nucleophilic solvent acetonitrile for the glycosylation reactions promoted by silver triflate with participating protecting groups in the 2-position of the glycosyl donor.