(R)-4-benzyl-3-[(2R,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyloct-6-enoyl]oxazolidin-2-one | 1447732-00-4

• 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-[(2R,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyloct-6-enoyl]oxazolidin-2-one
• 英文别名: (2'R,3'S,4'S,6E,4R)-3-[(3-[tert-butyldimethylsilyloxy]-2,4,6-trimethyl-1-oxo-oct-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone
• CAS: 1447732-00-4
• 化学式: C₂₇H₄₃NO₄Si
• 分子量: 473.728
• InChiKey: BHQUYSWICLPPCX-HFZSOHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 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-[(2R,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyloct-6-enoyl]oxazolidin-2-one 在 锂硼氢 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 4.0h， 以78%的产率得到(2S,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-oct-6-en-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of the C13–32 spiroacetal fragment of spirangien A

  摘要：

  Stereoselective synthesis of an advanced intermediate towards the highly cytotoxic polyketide metabolite spirangien A was achieved. A key step in the synthesis was installation of the C23 stereocentre by a substrate controlled C22-23 aldol reaction. Comparison of this result with previous literature reports suggests that the facial preference of the aldehyde controls the outcome of the C22-23 aldol coupling and depends on the 027/25 protecting groups when reacting with complex ketones, which contain the C17-15 stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.012
• 作为产物：
  描述：

  (2R,4E)-methyl 2,4-dimethyl-hex-4-enoate 在 2,6-二甲基吡啶 、 三氟甲磺酸二丁硼 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (R)-4-benzyl-3-[(2R,3S,4S,6E)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyloct-6-enoyl]oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of the C13–32 spiroacetal fragment of spirangien A

  摘要：

  Stereoselective synthesis of an advanced intermediate towards the highly cytotoxic polyketide metabolite spirangien A was achieved. A key step in the synthesis was installation of the C23 stereocentre by a substrate controlled C22-23 aldol reaction. Comparison of this result with previous literature reports suggests that the facial preference of the aldehyde controls the outcome of the C22-23 aldol coupling and depends on the 027/25 protecting groups when reacting with complex ketones, which contain the C17-15 stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.012

文献信息

• Electrocyclization of Oxatrienes in the Construction of Structurally Complex Pyranopyridones
  作者：Anna D. Fotiadou、Alexandros L. Zografos

  DOI：10.1021/ol3026457

  日期：2012.11.16

  Application of a tandem Knoevenagel/6 pi-electrocyclization sequence is able to produce highly substituted pyranopyridones from moderate to high yields in a one-step reaction. High diasteroselectivity is observed in some cases and was rationalized on the basis of the thermodynamic control of the evidenced reversibility of a 6 pi-electrocyclization reaction. Numerous examples are provided establishing a novel entry in natural product-like structures of pyranopyridone alkaloids.