Crystal structure and absolute configuration of (4 S,5 R,6 S)-4,5,6-trihy-droxy-3-methyl-cyclo-hex-2-enone (gabosine H)

Acta Crystallogr E Crystallogr Commun. 2017 Mar 28;73(Pt 4):606-609. doi: 10.1107/S2056989017004509. eCollection 2017 Apr 1.

Abstract

The mol-ecule of the title keto carbasugar, C7H10O4, is formed by a cyclo-hexene skeleton with an envelope conformation, substituted by carbonyl, methyl and hydroxyl groups. The crystal structure is controlled mainly by a combination of strong O-H⋯O and weak C-H⋯O hydrogen bonds, forming nearly perpendicular chains running parallel to the [110] and [-110] directions. This perpendicularity is caused by a tetra-gonal pseudosymmetry influenced by the similarity between the a and b axes, the value of 90.9770 (10)° of the β angle and the action of a 21 screw axis, which transform each chain into its corresponding nearly orthogonal one.

Keywords: Mitsunobu inversion reaction; absolute configuration; crystal structure; natural product.