tert-butyl-[4-[(3R,5R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)methoxy]-3-phenylmethoxyicosa-1,9-diynyl]phenoxy]-dimethylsilane | 1025446-83-6

• 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: tert-butyl-[4-[(3R,5R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)methoxy]-3-phenylmethoxyicosa-1,9-diynyl]phenoxy]-dimethylsilane
• CAS: 1025446-83-6
• 化学式: C₅₃H₈₀O₅Si₂
• 分子量: 853.386
• InChiKey: DCOLTBKSPHKDPK-FRAWRBJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  60
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-[4-[(3R,5R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)methoxy]-3-phenylmethoxyicosa-1,9-diynyl]phenoxy]-dimethylsilane 在 镍 氢气 作用下， 以 乙醇 为溶剂， 55.0 ℃ 、137.9 kPa 条件下， 反应 18.0h， 以88%的产率得到(3S,5R,7R)-5-O-(4-methoxybenzyl)-7-O-tert-butyldimethylsilyl-1-(4-tert-butyldimethylsilyloxyphenyl)icosane-3,5,7-triol
  参考文献：
  名称：

  A Carbohydrate-Based Approach for the Total Synthesis of Aculeatin D and 6-epi-Aculeatin D

  摘要：

  A concise approach for the total synthesis of aculeatin D and 6-epi-aculeatin D employing differentially protected anti,anti-1,3,5-triol alkyne prepared from alpha-D-glucoheptonic-gamma-lactone derivative is documented. Phenol protecting group manipulation for selective O-debenzylation during the hydrogenation of the diyne intermediate and one-pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total synthesis.

  DOI：

  10.1021/jo800026n
• 作为产物：
  描述：

  tert-butyl-[(3R,5R,7R)-5-[(4-methoxyphenyl)methoxy]-3-phenylmethoxyicosa-1,9-diyn-7-yl]oxy-dimethylsilane 、 4-碘叔丁基二甲基硅氧基苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 焦磷酸硫胺素 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以88%的产率得到tert-butyl-[4-[(3R,5R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)methoxy]-3-phenylmethoxyicosa-1,9-diynyl]phenoxy]-dimethylsilane
  参考文献：
  名称：

  A Carbohydrate-Based Approach for the Total Synthesis of Aculeatin D and 6-epi-Aculeatin D

  摘要：

  A concise approach for the total synthesis of aculeatin D and 6-epi-aculeatin D employing differentially protected anti,anti-1,3,5-triol alkyne prepared from alpha-D-glucoheptonic-gamma-lactone derivative is documented. Phenol protecting group manipulation for selective O-debenzylation during the hydrogenation of the diyne intermediate and one-pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total synthesis.

  DOI：

  10.1021/jo800026n

文献信息

• A Carbohydrate-Based Approach for the Total Synthesis of Aculeatin D and 6-<i>epi</i>-Aculeatin D
  作者：C. V. Ramana、Burgula Srinivas

  DOI：10.1021/jo800026n

  日期：2008.5.1

  A concise approach for the total synthesis of aculeatin D and 6-epi-aculeatin D employing differentially protected anti,anti-1,3,5-triol alkyne prepared from alpha-D-glucoheptonic-gamma-lactone derivative is documented. Phenol protecting group manipulation for selective O-debenzylation during the hydrogenation of the diyne intermediate and one-pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total synthesis.