110797-37-0Relevant academic research and scientific papers
A 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 structures
Kakita, Kosuke,Tsuda, Toshifumi,Suzuki, Noritoshi,Nakamura, Seiichi,Nambu, Hisanori,Hashimoto, Shunichi
experimental part, p. 5005 - 5017 (2012/08/28)
TMSOTf-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.
Building Units of Oligosaccharides, LXXXVI1). - Glycosidation with Thioglycosides of Oligosaccharides to Segments of O-Glycoproteins.
Paulsen, Hans,Rauwald, Wolfgang,Weichert, Udo
, p. 75 - 86 (2007/10/02)
In the presence of dimethyl(methylthio)sulfonium triflate (DMTST) thioglycosides of mono-, di-, tri-, and tetrasaccharides, which contain a 2-azido-2-deoxy-D-galactose as reducing unit, can react with the hydroxy group of selectively blocked derivatives of L-serine.These reactions yield the corresponding O-glycosides.Preferentially the α-glycosidically bound products will be obtained.In this way the trisaccharide glycoside 46 was prepared, which represents the core-II structure of mucins α-glycosidically linked to L-serine.Methyl triflate as promoter of this thioglycosidation is less efficient than DMTST.
