(4R)-4-Acetyl-3-(methoxymethyl)-2-oxothiazolidine | 143397-36-8

• 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-Acetyl-3-(methoxymethyl)-2-oxothiazolidine
• 英文别名: (4R)-4-acetyl-3-(methoxymethyl)-1,3-thiazolidin-2-one
• CAS: 143397-36-8
• 化学式: C₇H₁₁NO₃S
• 分子量: 189.235
• InChiKey: OMTITUGZAVZNRF-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-4-Acetyl-3-(methoxymethyl)-2-oxothiazolidine 在 cerium(III) chloride 、 四丁基氟化铵 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 二甲基亚砜 为溶剂， 生成 (1R,4Z,7a'S,8E,10Z,12S,15R,17S)-5,12-dimethyl-7',7a'-dihydro-3'H,5'H-2,16-dioxaspiro[bicyclo[13.3.1]nonadecane-17,1'-thiazolo[3,4-c]oxazole]-4,8,10-triene-3,5'-dione
  参考文献：
  名称：

  Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer

  摘要：

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.

  DOI：

  10.1021/jo00046a008
• 作为产物：
  描述：

  甲基锂 、 Methyl (4R)-3-(Methoxymethyl)-2-oxo-4-thiazolidinecarboxylate 以 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到(4R)-4-Acetyl-3-(methoxymethyl)-2-oxothiazolidine
  参考文献：
  名称：

  Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer

  摘要：

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.

  DOI：

  10.1021/jo00046a008

文献信息

• Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer
  作者：James D. White、Motoji Kawasaki

  DOI：10.1021/jo00046a008

  日期：1992.9

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.