(4R)-4-benzyl-3-[(2R,3S,4R)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentanoyl]-1,3-oxazolidin-2-one | 1513700-49-6

• 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)-4-benzyl-3-[(2R,3S,4R)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentanoyl]-1,3-oxazolidin-2-one
• CAS: 1513700-49-6
• 化学式: C₂₃H₃₇NO₅Si
• 分子量: 435.636
• InChiKey: GBGKYNSBPBJHFH-LFGUQSLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(2R,3S,4R)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentanoyl]-1,3-oxazolidin-2-one 在 2,6-二甲基吡啶 、 三甲基铝 、 叔丁基锂 、 二异丁基氢化铝 、 magnesium bromide ethyl etherate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 23.5h， 生成
  参考文献：
  名称：

  Synthesis of Angiolam A

  摘要：

  The first total synthesis of angiolam A has been accomplished in 18 steps. Key steps include vinylogous Mukaiyama aldol reactions of aldehyde-derived dienol ethers, conjugate reduction of the resulting double bond followed by diastereoselective protonation and the Witzeman protocol for macrolactamization. Comparison of the optical rotation of the synthesized material with the isolation data established that the absolute configuration of angiolam A is opposite from the proposed structure.

  DOI：

  10.1021/ol403423r
• 作为产物：
  描述：

  (2S)-3-[[(叔丁基)二甲基硅烷基]氧基]-2-甲基-1-丙醇 在 草酰氯 、 三氟甲磺酸二丁硼 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.42h， 生成 (4R)-4-benzyl-3-[(2R,3S,4R)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of Angiolam A

  摘要：

  The first total synthesis of angiolam A has been accomplished in 18 steps. Key steps include vinylogous Mukaiyama aldol reactions of aldehyde-derived dienol ethers, conjugate reduction of the resulting double bond followed by diastereoselective protonation and the Witzeman protocol for macrolactamization. Comparison of the optical rotation of the synthesized material with the isolation data established that the absolute configuration of angiolam A is opposite from the proposed structure.

  DOI：

  10.1021/ol403423r

文献信息

• Synthesis of Angiolam A
  作者：Marc Timo Gieseler、Markus Kalesse

  DOI：10.1021/ol403423r

  日期：2014.1.17

  The first total synthesis of angiolam A has been accomplished in 18 steps. Key steps include vinylogous Mukaiyama aldol reactions of aldehyde-derived dienol ethers, conjugate reduction of the resulting double bond followed by diastereoselective protonation and the Witzeman protocol for macrolactamization. Comparison of the optical rotation of the synthesized material with the isolation data established that the absolute configuration of angiolam A is opposite from the proposed structure.