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(2S,3S)-2,6-dimethylheptane-1,3-diol, the oxygenated side chain of 22(S)-hydroxycholestrol, and its synthetic precursor (R)-4-benzyl-3-[(2R,3S)-3-hydroxy-2,6-dimethylheptanoyl]-1,3-oxazolidin-2-one.

Authors
  • Høgmoen Åstrand, Ove Alexander
  • Iqbal, Zeshan
  • Sandberg, Marcel
  • Kase, Eili T
  • Görbitz, Carl Henrik
  • Rongved, Pål
Type
Published Article
Journal
Acta Crystallographica Section C Crystal Structure Communications
Publisher
International Union of Crystallography
Publication Date
Jun 01, 2013
Volume
69
Issue
Pt 6
Pages
647–650
Identifiers
DOI: 10.1107/S0108270113011852
PMID: 23744388
Source
Medline
License
Unknown

Abstract

(2S,3S)-2,6-dimethylheptane-1,3-diol, C9H20O2, (I), was synthesized from the ketone (R)-4-benzyl-3-[(2R,3S)-3-hydroxy-2,6-dimethylheptanoyl]-1,3-oxazolidin-2-one, C19H27NO4, (II), containing C atoms of known chirality. In both structures, strong hydrogen bonds between the hydroxy groups form tape motifs. The contribution from weaker C-H···O hydrogen bonds is much more evident in the structure of (II), which furthermore contains an example of a direct short Osp(3)···Csp(2) contact that represents a usually unrecognized type of intermolecular interaction.

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