(R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one | 1239664-46-0

• 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: (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one
• CAS: 1239664-46-0
• 化学式: C₂₁H₃₃NO₄Si
• 分子量: 391.583
• InChiKey: UJJCSILQZFBGGF-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one 在 锂硼氢 、 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 ethyl (2E,4E,6R)-6-(tert-butyldimethylsilyloxymethyl)octa-2,4-dienoate
  参考文献：
  名称：

  Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

  摘要：

  A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

  DOI：

  10.1021/ol402820d
• 作为产物：
  描述：

  (R)-3-(1-butyryl)-4-benzyloxazolidine-2-one 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 四氯化钛 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 32.17h， 生成 (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one
  参考文献：
  名称：

  Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

  摘要：

  A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

  DOI：

  10.1021/ol402820d

文献信息

• Evans, David A.; Welch, Dennie S.; Speed, Alexander W. H., Journal of the American Chemical Society, 2009, vol. 131, p. 3840 - 3841
  作者：Evans, David A.、Welch, Dennie S.、Speed, Alexander W. H.、Moniz, George A.、Reichelt, Andreas、Ho, Stephen

  DOI：——

  日期：——