(4R,5S)-1-[(2R,3S,6S)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-3-methyloxan-2-yl]-3,4-dimethyl-5-phenylimidazolidin-2-one | 943253-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-1-[(2R,3S,6S)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-3-methyloxan-2-yl]-3,4-dimethyl-5-phenylimidazolidin-2-one
• CAS: 943253-21-2
• 化学式: C₃₆H₄₈N₂O₃Si
• 分子量: 584.874
• InChiKey: SPIFOLZBQOGWPW-CESONASMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-1-[(2R,3S,6S)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-3-methyloxan-2-yl]-3,4-dimethyl-5-phenylimidazolidin-2-one 在 溴化锡 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2R)-2-[(2S,5S,6S)-6-[(2R)-but-3-en-2-yl]-5-methyloxan-2-yl]propan-1-ol 、 (2R)-2-[(2S,5S,6S)-6-[(2S)-but-3-en-2-yl]-5-methyloxan-2-yl]propan-1-ol
  参考文献：
  名称：

  A Formal Total Synthesis of (+)-Zincophorin. Observation of an Unusual Urea-Directed Stork−Crabtree Hydrogenation

  摘要：

  A formal total synthesis of (+)-zincophorin via interception of Miyashita's advanced intermediates is described here. This effort features the first synthetic application of an inverse demand hetero [4 + 2] cycloaddition of a chiral allenamide, and the observation of an unusual urea directed Stork-Crabtree hydrogenation.

  DOI：

  10.1021/ol070791a
• 作为产物：
  描述：

  (4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-methylpent-1-en-3-ol 在 platinum on activated charcoal 、 5% platinum on alumina sodium tetrahydroborate 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， -78.0~80.0 ℃ 、10.34 MPa 条件下， 反应 122.0h， 生成 (4R,5S)-1-[(2R,3S,6S)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-3-methyloxan-2-yl]-3,4-dimethyl-5-phenylimidazolidin-2-one
  参考文献：
  名称：

  A Formal Total Synthesis of (+)-Zincophorin. Observation of an Unusual Urea-Directed Stork−Crabtree Hydrogenation

  摘要：

  A formal total synthesis of (+)-zincophorin via interception of Miyashita's advanced intermediates is described here. This effort features the first synthetic application of an inverse demand hetero [4 + 2] cycloaddition of a chiral allenamide, and the observation of an unusual urea directed Stork-Crabtree hydrogenation.

  DOI：

  10.1021/ol070791a

文献信息

• Studies on a Urea-Directed Stork−Crabtree Hydrogenation. Synthesis of the C1−C9 Subunit of (+)-Zincophorin
  作者：Zhenlei Song、Richard P. Hsung、Ting Lu、Andrew G. Lohse

  DOI：10.1021/jo7017922

  日期：2007.12.1

  [GRAPHICS]A detailed account on the stereoselective synthesis of the C1-C9 subunit of (+)-zincophorin is described here. This approach features the first application of a stereoselective inverse electron demand hetero-[4 + 2] cycloaddition of chiral allenamides in natural product synthesis. The C1-C9 subunit matches Cossy's intermediate, thereby constituting a formal total synthesis. In addition, details of an unusual urea-directed Stork-Crabtree hydrogenation observed during these efforts are also disclosed here.