Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 4 (April 2009)

organic compounds

Acta Cryst. (2009). C65, o151-o154 [ doi:10.1107/S0108270109008294 ]

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

V. Langer, B. Steiner and M. Koós

Abstract: In the title compounds, C₁₂H₂₀O₆, (I), and C₉H₁₆O₆, (II), the five-membered furanose ring adopts a ⁴T₃ conformation and the five-membered 1,3-dioxolane ring adopts an E₃ conformation. The six-membered 1,3-dioxane ring in (I) adopts an almost ideal ^OC₃ conformation. The hydrogen-bonding patterns for these compounds differ substantially: (I) features just one intramolecular O-HO hydrogen bond [OO = 2.933 (3) Å], whereas (II) exhibits, apart from the corresponding intramolecular O-HO hydrogen bond [OO = 2.7638 (13) Å], two intermolecular bonds of this type [OO = 2.7708 (13) and 2.7730 (12) Å]. 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 -CH₂OH group at the C1-furanose position by another group can considerably affect the conformation of the 1,3-dioxolane ring.

Formula: C₁₂H₂₀O₆ and C₉H₁₆O₆


	Structure factor file (CIF format) (73.2 kbytes) [ doi:10.1107/S0108270109008294/gg3193Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (109.1 kbytes) [ doi:10.1107/S0108270109008294/gg3193IIsup3.hkl ] Contains datablock II

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