title: (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.
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.
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, PO Box 1068 Blindern, N-0316 Oslo, Norway.
authors.forename: Ove Alexander
authors.initials: OA
authors.lastname: Høgmoen Åstrand
authors.forename: Zeshan
authors.initials: Z
authors.lastname: Iqbal
authors.forename: Marcel
authors.initials: M
authors.lastname: Sandberg
authors.forename: Eili T
authors.initials: ET
authors.lastname: Kase
authors.forename: Carl Henrik
authors.initials: CH
authors.lastname: Görbitz
authors.forename: Pål
authors.initials: P
authors.lastname: Rongved
mesh_terms: D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D006018:Glycols / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D006888:Hydroxycholesterols / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006018:Glycols; D006888:Hydroxycholesterols; D023303:Oxazolidinones; C003585:22-hydroxycholesterol