Convenient synthesis of O-(2-acitamido-2-deoxy-β- D -glucopyranosyl)-serine and -threonine building blocks for solid-phase glycopeptide assembly
1994; Issue: 18 Linguagem: Inglês
10.1039/p19940002615
ISSN2050-8255
AutoresAntonio Vargas‐Berenguel, Morten Meldal, Hans Paulsen, Klaus Bock,
Tópico(s)Chemical Synthesis and Analysis
ResumoThe 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.
Referência(s)