title: Orthogonally protected D-galactosamine thioglycoside building blocks via highly regioselective, double serial and double parallel inversions of β-D-thiomannoside.
abstract: An efficient route for the synthesis of orthogonally protected D-galactosamine thioglycosides via one-pot double serial and double parallel displacements of the D-mannosyl-2,4-bis-trifluoromethanesulfonates by azide and nitrite ions is described. These building blocks were utilized to synthesize the rare disaccharide moiety of the zwitterionic polysaccharide of Bacteroides fragilis and the selectively protected Tn antigen.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India.
authors.forename: Madhu
authors.initials: M
authors.lastname: Emmadi
authors.forename: Suvarn S
authors.initials: SS
authors.lastname: Kulkarni
mesh_terms: D001441:Bacteroides fragilis / Q000737:chemistry; D002236:Carbohydrate Conformation; D005688:Galactosamine / Q000737:chemistry*; D008358:Mannose / Q000031:analogs & derivatives / Q000737:chemistry*; D013237:Stereoisomerism; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013865:Thioglycosides; D005688:Galactosamine; D008358:Mannose