(S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone | 1440534-69-9

• 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: (S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone
• 英文别名: (4S)-4-benzyl-3-[(E,4S,5R)-5-hydroxy-2,4-dimethylhex-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 1440534-69-9
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: ODMRFQIUDFFIFN-QOZMNAKESA-N

物化性质

• 沸点：
  453.2±47.0 °C(predicted)
• 密度：
  1.186±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone 在 咪唑 、 三乙基硅烷 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 tin(II) trifluoromethanesulfonate 、 lithium hydroxide monohydrate 、 (R)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine 、 palladium 10% on activated carbon 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 copper(l) chloride 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 127.34h， 生成 (6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid
  参考文献：
  名称：

  Formal Total Synthesis of Lactimidomycin

  摘要：

  A concise synthesis of an intermediate of lactimidomycin, a glutarimide-containing macrocyclic polyketide produced by an actinomycete, has been accomplished in 35% overall yield from a known vinylketene silyl N,O-acetal by a 10-step sequence that involves two types of asymmetric aldol reactions to install all the stereocenters, the Stille coupling to set up the whole carbon famework, and the Yamaguchi lactonization to construct the 12-membered macrolactone ring.

  DOI：

  10.1021/ol401214f
• 作为产物：
  描述：

  (S)-4-benzyl-3-{(1E,3E)-1[(tert-butyldimethylsilyl)oxy]-2-methylpenta-1,3-diene-1-yl}oxazolidin-2-one 、 乙醛 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以92%的产率得到(S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone
  参考文献：
  名称：

  Formal Total Synthesis of Lactimidomycin

  摘要：

  A concise synthesis of an intermediate of lactimidomycin, a glutarimide-containing macrocyclic polyketide produced by an actinomycete, has been accomplished in 35% overall yield from a known vinylketene silyl N,O-acetal by a 10-step sequence that involves two types of asymmetric aldol reactions to install all the stereocenters, the Stille coupling to set up the whole carbon famework, and the Yamaguchi lactonization to construct the 12-membered macrolactone ring.

  DOI：

  10.1021/ol401214f

文献信息

• Development of the Synthesis of Desepoxy-Tedanolide C
  作者：Daniel Lücke、Markus Kalesse

  DOI：10.1021/acs.joc.3c02437

  日期：2024.2.16

  We are presenting the development of our route for the total synthesis of desepoxy-tedanolide C. Through the obtained analytical data, the proposed structure of tedanolide C is questioned and a different configuration for this natural product is proposed. Key steps of the synthesis are a Kiyooka aldol reaction that builds up the tertiary alcohol flanked by three oxygenated carbon atoms and two aldol

  我们正在介绍我们的去环氧-tedanolide C 全合成路线的开发。通过获得的分析数据，对 tedanolide C 的拟议结构提出了质疑，并提出了这种天然产物的不同构型。合成的关键步骤是 Kiyooka 羟醛反应，该反应生成侧翼有三个含氧碳原子的叔醇，以及两个用于片段偶联的羟醛反应。 Julia-Kocienski 烯化用于侧链的安装。除了成功的合成之外，还详细描述了西南半球保护基团设置的发展以及构建目标分子的另一种逆合成尝试。
• Formal Total Synthesis of Lactimidomycin
  作者：Tomohiro Nagasawa、Shigefumi Kuwahara

  DOI：10.1021/ol401214f

  日期：2013.6.21

  A concise synthesis of an intermediate of lactimidomycin, a glutarimide-containing macrocyclic polyketide produced by an actinomycete, has been accomplished in 35% overall yield from a known vinylketene silyl N,O-acetal by a 10-step sequence that involves two types of asymmetric aldol reactions to install all the stereocenters, the Stille coupling to set up the whole carbon famework, and the Yamaguchi lactonization to construct the 12-membered macrolactone ring.