[(2S,3R)-3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxiran-2-yl]methanol | 1434626-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R)-3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxiran-2-yl]methanol
• CAS: 1434626-54-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: ODXIMVDJNRYWIB-XAVMHZPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2S,3R)-3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxiran-2-yl]methanol 在 吡啶 、 2,6-二甲基吡啶 、 甲醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 (2R,3R)-3-((tert-butyldimethylsilyl)oxy)-3-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-methoxypropyl pivalate
  参考文献：
  名称：

  Epi-, Epoxy-, and C2-Modified Bengamides: Synthesis and Biological Evaluation

  摘要：

  With the objective of investigating the influence of structural modifications of the polyketide chain of the bengamides upon their antitumoral activities, we targeted the preparation of bengamide E analogues with modification of the stereochemistry at C-2 and at C-3, the substituent at the C-2 position, and the presence of oxirane rings. For the synthesis of these analogues, a new synthetic method for asymmetric epoxidation, developed in our laboratories, was employed utilizing the chiral sulfonium salts 22 and 23. In order to access 2-epi-bengamide E from these epoxy amides, a synthetic methodology, developed by Miyashita, allowed an oxirane-ring-opening reaction with a double inversion of the configuration. Alternatively, an aldol reaction provided access to the same analogue in a shorter and more efficient manner. Finally, biological evaluation of all of these bengamide E analogues demonstrated that the polyketide chain is essential for the antitumor activity of these natural products, not being amenable to structural or configurational modifications.

  DOI：

  10.1021/jo4003272
• 作为产物：
  描述：

  2,3-O-isopropylidene-D-threo-4-pentenose 在 三乙基硼氢化锂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 1.0h， 生成 [(2S,3R)-3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxiran-2-yl]methanol
  参考文献：
  名称：

  Epi-, Epoxy-, and C2-Modified Bengamides: Synthesis and Biological Evaluation

  摘要：

  With the objective of investigating the influence of structural modifications of the polyketide chain of the bengamides upon their antitumoral activities, we targeted the preparation of bengamide E analogues with modification of the stereochemistry at C-2 and at C-3, the substituent at the C-2 position, and the presence of oxirane rings. For the synthesis of these analogues, a new synthetic method for asymmetric epoxidation, developed in our laboratories, was employed utilizing the chiral sulfonium salts 22 and 23. In order to access 2-epi-bengamide E from these epoxy amides, a synthetic methodology, developed by Miyashita, allowed an oxirane-ring-opening reaction with a double inversion of the configuration. Alternatively, an aldol reaction provided access to the same analogue in a shorter and more efficient manner. Finally, biological evaluation of all of these bengamide E analogues demonstrated that the polyketide chain is essential for the antitumor activity of these natural products, not being amenable to structural or configurational modifications.

  DOI：

  10.1021/jo4003272

文献信息

• <i>Epi</i>-, Epoxy-, and C2-Modified Bengamides: Synthesis and Biological Evaluation
  作者：Francisco Sarabia、Francisca Martín-Gálvez、Cristina García-Ruiz、Antonio Sánchez-Ruiz、Carlos Vivar-García

  DOI：10.1021/jo4003272

  日期：2013.6.7

  With the objective of investigating the influence of structural modifications of the polyketide chain of the bengamides upon their antitumoral activities, we targeted the preparation of bengamide E analogues with modification of the stereochemistry at C-2 and at C-3, the substituent at the C-2 position, and the presence of oxirane rings. For the synthesis of these analogues, a new synthetic method for asymmetric epoxidation, developed in our laboratories, was employed utilizing the chiral sulfonium salts 22 and 23. In order to access 2-epi-bengamide E from these epoxy amides, a synthetic methodology, developed by Miyashita, allowed an oxirane-ring-opening reaction with a double inversion of the configuration. Alternatively, an aldol reaction provided access to the same analogue in a shorter and more efficient manner. Finally, biological evaluation of all of these bengamide E analogues demonstrated that the polyketide chain is essential for the antitumor activity of these natural products, not being amenable to structural or configurational modifications.