2024-03-28T18:00:38Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/496712022-11-17T02:08:08Zhdl_2115_20044hdl_2115_124A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structuresKakita, KosukeTsuda, ToshifumiSuzuki, NoritoshiNakamura, SeiichiNambu, HisanoriHashimoto, ShunichiCarbohydratesGlycosylationTN-antigenMucinPhosphates499TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of α-selectivity (α/β=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides.ElsevierJournal Articleapplication/pdfhttp://hdl.handle.net/2115/49671https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/49671/1/Tet68-25_5005-5017.pdf0040-4020Tetrahedron6825500550172012-06-24enginfo:doi/10.1016/j.tet.2012.04.059author