methyl (2S,4S)-5,5-dichloro-2-[[(2S,4S)-5,5-dichloro-4-methyl-2-[methyl(phenylmethoxycarbonyl)amino]pentanoyl]-methylamino]-4-methylpentanoate | 916675-85-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,4S)-5,5-dichloro-2-[[(2S,4S)-5,5-dichloro-4-methyl-2-[methyl(phenylmethoxycarbonyl)amino]pentanoyl]-methylamino]-4-methylpentanoate
• CAS: 916675-85-9
• 化学式: C₂₃H₃₂Cl₄N₂O₅
• 分子量: 558.329
• InChiKey: KLTJINUMIMSYLB-LAQRGFTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S)-5,5-dichloro-2-[[(2S,4S)-5,5-dichloro-4-methyl-2-[methyl(phenylmethoxycarbonyl)amino]pentanoyl]-methylamino]-4-methylpentanoate 在 N-甲基吗啉 、 氢溴酸 、 溶剂黄146 作用下， 以 仲丁醇 为溶剂， 反应 3.0h， 生成 dysamide B
  参考文献：
  名称：

  Total Synthesis of the Chlorinated Marine Natural Product Dysamide B

  摘要：

  [GRAPHICS]Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.

  DOI：

  10.1021/ol062279f
• 作为产物：
  描述：

  (2S,4S)-5,5-dichloroleucine 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 sodium hydride 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 methyl (2S,4S)-5,5-dichloro-2-[[(2S,4S)-5,5-dichloro-4-methyl-2-[methyl(phenylmethoxycarbonyl)amino]pentanoyl]-methylamino]-4-methylpentanoate
  参考文献：
  名称：

  Total Synthesis of the Chlorinated Marine Natural Product Dysamide B

  摘要：

  [GRAPHICS]Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.

  DOI：

  10.1021/ol062279f

文献信息

• Total Synthesis of the Chlorinated Marine Natural Product Dysamide B
  作者：Amanda C. Durow、G. Cliona Long、Susan J. O'Connel、Christine L. Willis

  DOI：10.1021/ol062279f

  日期：2006.11.9

  [GRAPHICS]Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.