Glycosylation of phenols: preparation of 1,2-cis and 1,2-trans glycosylated tyrosine derivatives to be used in solid-phase glycopeptide synthesis
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 17,p. 2119-2129
- https://doi.org/10.1039/p19930002119
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.Keywords
This publication has 0 references indexed in Scilit: