(4R)-4-benzyl-3-[(2R,3S)-3-hydroxy-2-methyloct-7-enoyl]-1,3-oxazolidin-2-one | 499992-34-6

• 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)-3-hydroxy-2-methyloct-7-enoyl]-1,3-oxazolidin-2-one
• CAS: 499992-34-6
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: OOJDHVHTIVRDGS-OIISXLGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (4R)-4-benzyl-3-[(2R,3S)-3-hydroxy-2-methyloct-7-enoyl]-1,3-oxazolidin-2-one 在 2,6-二甲基吡啶 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 三甲基铝 、 sodium hexamethyldisilazane 、 臭氧 、 N,N-二异丙基乙胺 、 lithium chloride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 19.7h， 生成
  参考文献：
  名称：

  Approach to the Tricyclic Core of the Tigliane–Daphnane Diterpenes. Concerning the Utility of Transannular Aldol Additions

  摘要：

  Two transannular (TA) aldol reactions were used to assemble the tricyclic carbon skeleton found in the tigliane and daphnane classes of diterpene natural products.

  DOI：

  10.1021/ol401367h
• 作为产物：
  描述：

  5-己烯醛 、 (R)-(-)-4-苄基-3-丙酰基-2-恶唑烷酮 在 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(4R)-4-benzyl-3-[(2R,3S)-3-hydroxy-2-methyloct-7-enoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Diastereoselective Synthesis of the Pectenotoxin 2 Non-Anomeric AB Spiroacetal

  摘要：

  The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity.

  DOI：

  10.1021/ol0630447

文献信息

• A Spirodiepoxide-Based Strategy to the A−B Ring System of Pectenotoxin 4
  作者：Stephen D. Lotesta、Yongquan Hou、Lawrence J. Williams

  DOI：10.1021/ol063087n

  日期：2007.3.1

  A synthesis of a pectenotoxin 4 C1-C15 segment is reported. Suitable C1-C7 and C8-C15 segments were prepared, coupled, converted to I and the C3-hydroxy variant, and then cyclized. Key findings include the stereoselective conversion of the allene to the corresponding spirodiepoxide, oxidative cleavage of the p-methoxybenzyl ether, and cyclization of the spirodiepoxide to spiroketal II.
• Approach to the Tricyclic Core of the Tigliane–Daphnane Diterpenes. Concerning the Utility of Transannular Aldol Additions
  作者：Arthur J. Catino、Alexandra Sherlock、Peyton Shieh、Joseph S. Wzorek、David A. Evans

  DOI：10.1021/ol401367h

  日期：2013.7.5

  Two transannular (TA) aldol reactions were used to assemble the tricyclic carbon skeleton found in the tigliane and daphnane classes of diterpene natural products.
• Diastereoselective Synthesis of the Pectenotoxin 2 Non-Anomeric AB Spiroacetal
  作者：Danielle Vellucci、Scott D. Rychnovsky

  DOI：10.1021/ol0630447

  日期：2007.2.1

  The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity.