title: Tuneable regioselectivity during the mono-etherification of the 2,3-diol of a mannose derivative.
abstract: The paper reports selective mono-etherification of the 2-, and 3-hydroxyl groups of methyl 4,6-O-isopropylidene-α-d-mannopyranoside using tin(II) chloride catalysed reactions of diaryldiazomethanes. By the use of different diazo compounds and the variation of the tin(II) chloride concentration the ether formation can be shifted from over 90% 3-selectivity to over 90% 2-selectivity.
authors.affiliation: Faculty of Natural Resourse Sciences, University of Akureyri, 600 Akureyri, Iceland. Electronic address: sigthor@unak.is.
authors.forename: Sigthor
authors.initials: S
authors.lastname: Petursson
authors.affiliation: Faculty of Natural Resourse Sciences, University of Akureyri, 600 Akureyri, Iceland.
authors.forename: Sean M
authors.initials: SM
authors.lastname: Scully
authors.affiliation: Science Institute, University of Iceland, Dunhagi 3, 107 Reykjavík, Iceland.
authors.forename: Sigridur
authors.initials: S
authors.lastname: Jonsdottir
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D008766:Methylmannosides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D008766:Methylmannosides; D017971:Tin Compounds; C023599:stannous chloride
keywords: Catalysis; Diol; Protection; Regioselectivity; Tin(II) chloride