2,3:4,6-Di-O-isopropylidene-alpha-L-sorbofuranose and 2,3-O-isopropylidene-alpha-L-sorbofuranose. 2009

Vratislav Langer, and Bohumil Steiner, and Miroslav Koós
Environmental Inorganic Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, SE-412 96 Göteborg, Sweden. langer@chalmers.se

In the title compounds, C(12)H(20)O(6), (I), and C(9)H(16)O(6), (II), the five-membered furanose ring adopts a (4)T(3) conformation and the five-membered 1,3-dioxolane ring adopts an E(3) conformation. The six-membered 1,3-dioxane ring in (I) adopts an almost ideal (O)C(3) conformation. The hydrogen-bonding patterns for these compounds differ substantially: (I) features just one intramolecular O-H...O hydrogen bond [O...O = 2.933 (3) A], whereas (II) exhibits, apart from the corresponding intramolecular O-H...O hydrogen bond [O...O = 2.7638 (13) A], two intermolecular bonds of this type [O...O = 2.7708 (13) and 2.7730 (12) A]. This study illustrates both the similarity between the conformations of furanose, 1,3-dioxolane and 1,3-dioxane rings in analogous isopropylidene-substituted carbohydrate structures and the only negligible influence of the presence of a 1,3-dioxane ring on the conformations of furanose and 1,3-dioxolane rings. In addition, in comparison with reported analogs, replacement of the -CH(2)OH group at the C1-furanose position by another group can considerably affect the conformation of the 1,3-dioxolane ring.

UI MeSH Term Description Entries

Related Publications

Vratislav Langer, and Bohumil Steiner, and Miroslav Koós
August 2005, Carbohydrate research,
Vratislav Langer, and Bohumil Steiner, and Miroslav Koós
August 2006, Acta crystallographica. Section C, Crystal structure communications,
Vratislav Langer, and Bohumil Steiner, and Miroslav Koós
December 1966, Ceskoslovenska farmacie,
Vratislav Langer, and Bohumil Steiner, and Miroslav Koós
April 2011, Carbohydrate research,
Copied contents to your clipboard!