(1R,3R,4S,5S,6R,7S,8R,9S)-5,6,9-tris(tert-butyldimethylsilyloxy)-octahydro-7,8-dihydroxy-2,2-dimethylcycloocta[d][1,3]dioxol-4-yl 4-methoxybenzoate | 1056883-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3R,4S,5S,6R,7S,8R,9S)-5,6,9-tris(tert-butyldimethylsilyloxy)-octahydro-7,8-dihydroxy-2,2-dimethylcycloocta[d][1,3]dioxol-4-yl 4-methoxybenzoate
• CAS: 1056883-16-9
• 化学式: C₃₇H₆₈O₁₀Si₃
• 分子量: 757.197
• InChiKey: JVNFUTAJVUYIBT-QBKKKPARSA-N

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S,5S,6R,7S,8R,9S)-5,6,9-tris(tert-butyldimethylsilyloxy)-octahydro-7,8-dihydroxy-2,2-dimethylcycloocta[d][1,3]dioxol-4-yl 4-methoxybenzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成
  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
• 作为产物：
  描述：

  在 N-甲基吗啉 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (1R,3R,4S,5S,6R,7S,8R,9S)-5,6,9-tris(tert-butyldimethylsilyloxy)-octahydro-7,8-dihydroxy-2,2-dimethylcycloocta[d][1,3]dioxol-4-yl 4-methoxybenzoate
  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