N-Boc-D-Ser-Ile-OH | 1148056-71-6

• 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
• 英文名称: N-Boc-D-Ser-Ile-OH
• 英文别名: Boc-D-Ser-Ile-OH；(2S,3S)-2-[[(2R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-methylpentanoic acid
• CAS: 1148056-71-6
• 化学式: C₁₄H₂₆N₂O₆
• 分子量: 318.37
• InChiKey: FQVISSIQBVDBIZ-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  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

文献信息

• Asymmetric Total Synthesis and Stereochemical Revision of Gymnangiamide
  作者：Hitoshi Tone、Marie Buchotte、Céline Mordant、Eric Guittet、Tahar Ayad、Virginie Ratovelomanana-Vidal

  DOI：10.1021/ol900184d

  日期：2009.5.7

  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.