EFFICIENT SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-SER THR BUILDING-BLOCKS FOR SPPS OF O-GLCNAC GLYCOPEPTIDES/

Authors
MEINJOHANNS E MELDAL M BOCK K
Citation
E. Meinjohanns et al., EFFICIENT SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-SER THR BUILDING-BLOCKS FOR SPPS OF O-GLCNAC GLYCOPEPTIDES/, Tetrahedron letters, 36(50), 1995, pp. 9205-9208
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
50
Year of publication
1995
Pages
9205 - 9208
Database
ISI
SICI code
0040-4039(1995)36:50<9205:ESOO>2.0.ZU;2-P
Abstract
Suitably protected building blocks for solid-phase synthesis of beta-O -GlcNAc glycopeptides. N-alpha-Fmor-Ser(Ac-3-beta-D-GlcNAc)-OPfp 10 an d N-alpha-Fmoc-Thr(AL(3)-beta-D-GlcNAc)-OPfp 11 have been synthesized by stereoselective glycosylation of N-alpha-Fmoc-Ser-OPfE 6 and N-alph a-Fmoc-Thr-OPfp 7, respectively. with the 2-trichloroethoxycarbonylami no (Teoc) glycosyl donors 3 and 5, followed by in situ reduction of th e Teoc-group and simultaneous N-acetylation using zinc dust in tetrahy drofuranlacetic anhydridelacetic acid (3:2:1).