Convenient synthesis of O-(2-acitamido-2-deoxy-β-D-glucopyranosyl)-serine and -threonine building blocks for solid-phase glycopeptide assembly
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 18,p. 2615-2619
- https://doi.org/10.1039/p19940002615
Abstract
The suitably protected building blocks for solid-phase glycopeptide synthesis, Nα-Fmoc-Ser(Ac3-β-D-GlcNAc)-OPfp, 11, and Nα-Fmoc-Ther(Ac3-β-D-GlcNAc)-OPfp, 12, have been synthesized by stereo-selective glycosidation of the 2-allyloxycarbonylamino glycosyl donor 7 with Nα-Fmoc-Ser -OPfp, 3, and Nα-Fmoc-Thr -OPfp, 4, followed by Pdo-catalysed allyl transfer from the N-allyloxycarbonyl group in the presence of acetic anhydride.Keywords
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