(1S,3S,4R,5R,6R,7S,8R,9R)-5,6-bis(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)octahydro-7,8-dihydroxy-2,2-dimethylcycloocta[d][1,3]dioxol-9-yl acetate | 1056883-10-3

• 英文名称: (1S,3S,4R,5R,6R,7S,8R,9R)-5,6-bis(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)octahydro-7,8-dihydroxy-2,2-dimethylcycloocta[d][1,3]dioxol-9-yl acetate
• CAS: 1056883-10-3
• 化学式: C₃₃H₅₈O₁₀Si₂
• 分子量: 670.989
• InChiKey: IGHFIWSULWLSMW-WKARWUPSSA-N

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R,5R,6R,7S,8R,9R)-5,6-bis(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)octahydro-7,8-dihydroxy-2,2-dimethylcycloocta[d][1,3]dioxol-9-yl acetate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 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 (1S,3S,4R,5R,6R,7S,8R,9R)-5,6-bis(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)octahydro-7,8-dihydroxy-2,2-dimethylcycloocta[d][1,3]dioxol-9-yl acetate
  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