| 1148056-63-6

• 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
• CAS: 1148056-63-6
• 化学式: C₄₇H₇₁N₅O₁₂
• 分子量: 898.107
• InChiKey: ODELUMUVFGHWNN-UVLFGPBJSA-N

物化性质

• 沸点：
  1081.8±65.0 °C(predicted)
• 密度：
  1.197±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  64.0
• 可旋转键数：
  23.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  242.16
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 水 、 碳酸氢钠 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 以100%的产率得到benzyl (2S,3R)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((2S,3S)-2-((R)-2-amino-3-hydroxypropanamido)-3-methylpentanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-hydroxy-2-methylpropanamido)-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Asymmetric Total Synthesis and Stereochemical Revision of Gymnangiamide

  摘要：

  The asymmetric total synthesis of the originally proposed structure of gymnangiamide, a cytotoxic pentapeptide isolated from the marine hydroid Gymnangium regae Jaderholm, has been achieved. Key to the synthesis was the use of asymmetric hydrogenation of alpha-substituted, beta-ketoesters through dynamic kinetic resolution for the preparation of nonproteinogenic chiral amino acids. The disparity of the NMR spectra between the synthetic material containing the L-serine residue and the natural product required a revision of the proposed structure.

  DOI：

  10.1021/ol900184d
• 作为产物：
  描述：

  N-Boc-D-Ser-Ile-OH 、 benzyl (2S,3R)-2-[[(2R,3R)-3-[(2S)-1-[(3R,4S,5S)-4-amino-3-methoxy-5-methylheptanoyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoyl]amino]-3-hydroxy-3-phenylpropanoate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 14.0h， 以80%的产率得到
  参考文献：
  名称：

  Asymmetric Total Synthesis and Stereochemical Revision of Gymnangiamide

  摘要：

  The asymmetric total synthesis of the originally proposed structure of gymnangiamide, a cytotoxic pentapeptide isolated from the marine hydroid Gymnangium regae Jaderholm, has been achieved. Key to the synthesis was the use of asymmetric hydrogenation of alpha-substituted, beta-ketoesters through dynamic kinetic resolution for the preparation of nonproteinogenic chiral amino acids. The disparity of the NMR spectra between the synthetic material containing the L-serine residue and the natural product required a revision of the proposed structure.

  DOI：

  10.1021/ol900184d