(7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4.3.0]non-1-en-2-one | 769168-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4.3.0]non-1-en-2-one
• 英文别名: (5S,7R)-5,7-bis[[tert-butyl(diphenyl)silyl]oxy]-4,5,6,7-tetrahydro-3H-cyclopenta[c]pyran-1-one
• CAS: 769168-68-5
• 化学式: C₄₀H₄₆O₄Si₂
• 分子量: 646.974
• InChiKey: WECAVJWAPGWDKM-MPQUPPDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4.3.0]non-1-en-2-one 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以85%的产率得到(1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4.3.0]nonan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of (1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4,3,0]nonan-2-one

  摘要：

  The asymmetric synthesis of (1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4,3,0]nonan-2-one 1 from (4S)-4-acetoxy-2-methoxycarbonyl-3-methoxycarbonylmethyl-2-cyclopenten-1-one 2 is described in eight steps. Compound 2 was readily prepared from L-malic acid according to a known procedure. The key step of this synthesis is a palladium on charcoal catalyzed hydrogenation of olefinic bicyclic lactone 9. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.016
• 作为产物：
  描述：

  (9S)-9-acetoxy-7-methoxycarbonyl-8-methoxycarbonylmethyl-1,5-dithiaspiro[5.4]dec-7-ene 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 二异丁基氢化铝 、 sodium carbonate 、 高碘酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 51.8h， 生成 (7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4.3.0]non-1-en-2-one
  参考文献：
  名称：

  Asymmetric synthesis of (1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4,3,0]nonan-2-one

  摘要：

  The asymmetric synthesis of (1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4,3,0]nonan-2-one 1 from (4S)-4-acetoxy-2-methoxycarbonyl-3-methoxycarbonylmethyl-2-cyclopenten-1-one 2 is described in eight steps. Compound 2 was readily prepared from L-malic acid according to a known procedure. The key step of this synthesis is a palladium on charcoal catalyzed hydrogenation of olefinic bicyclic lactone 9. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.016

文献信息

• Asymmetric synthesis of (1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4,3,0]nonan-2-one
  作者：Xiao-Xin Shi、Wei He、Qing-Quan Wu、Jie Yin、Feng Ni、Xiao-Zhou Jin

  DOI：10.1016/j.tetasy.2004.06.016

  日期：2004.8

  The asymmetric synthesis of (1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4,3,0]nonan-2-one 1 from (4S)-4-acetoxy-2-methoxycarbonyl-3-methoxycarbonylmethyl-2-cyclopenten-1-one 2 is described in eight steps. Compound 2 was readily prepared from L-malic acid according to a known procedure. The key step of this synthesis is a palladium on charcoal catalyzed hydrogenation of olefinic bicyclic lactone 9. (C) 2004 Elsevier Ltd. All rights reserved.