(1r,2R,3R,4R,5s,6S,7S,8S)-cyclooctan-1,2,3,4,5,6,7,8-octol | 1056883-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1r,2R,3R,4R,5s,6S,7S,8S)-cyclooctan-1,2,3,4,5,6,7,8-octol
• CAS: 1056883-17-0
• 化学式: C₈H₁₆O₈
• 分子量: 240.21
• InChiKey: SHKMDTMTOGKSDM-NGTFYADESA-N

反应信息

• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (1r,2R,3R,4R,5s,6S,7S,8S)-cyclooctan-1,2,3,4,5,6,7,8-octol
  参考文献：
  名称：

  Contiguously Substituted Cyclooctane Polyols. Configurational Assignments via ¹H NMR Correlations and Symmetry Considerations

  摘要：

  More advanced oxidation of the cyclooctadienol shown, readily available in enantiomerically pure form from D-glucose, has given rise to a series of intermediates whose relative (and ultimately absolute) configuration was assigned on the basis of H-1/H-1 coupling constant analysis. The selectivities that were deduced in this manner were drawn from the sequential application of CrO3 oxidation in tandem with Luche reduction, two-step NMO-promoted osmylations bracketed by acetonide formation, and wholesale deprotection. The stereoselectivities of these reactions were traced by H-1 NMR spectroscopy, and the stereochemical assignments were confirmed by the presence or absence of symmetry in the final cyclooctane polyols (four shown) generated in this investigation.

  DOI：

  10.1021/jo801443d