title: Synthesis of a sucrose dimer with enone tether; a study on its functionalization.
abstract: The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions ('the glucose ends'). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was oxidized with osmium tetroxide to a diol. Absolute configurations of the allylic alcohol as well as the diol were determined by circular dichroism (CD) spectroscopy using the in situ dimolybdenum methodology.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Pakulski
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Norbert
authors.initials: N
authors.lastname: Gajda
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Jawiczuk
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Jadwiga
authors.initials: J
authors.lastname: Frelek
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Cmoch
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Sławomir
authors.initials: S
authors.lastname: Jarosz
keywords: CD-spectroscopy; Cotton effect; multivalent glycosystems; osmylation; stereoselective synthesis; sucrose