allyl 4(S)-[(tert-butoxycarbonyl)-amino]-3(R)-hydroxy-5-methylheptanoate | 1088711-89-0

• 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: allyl 4(S)-[(tert-butoxycarbonyl)-amino]-3(R)-hydroxy-5-methylheptanoate
• 英文别名: (3R,4S,5S)-allyl 4-(tert-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate；prop-2-enyl (3R,4S,5S)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoate
• CAS: 1088711-89-0
• 化学式: C₁₆H₂₉NO₅
• 分子量: 315.41
• InChiKey: DMFDBQKOIUXBHH-SCRDCRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 4(S)-[(tert-butoxycarbonyl)-amino]-3(R)-hydroxy-5-methylheptanoate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.34h， 生成 (5S,8S,11S,12R)-allyl 11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-12-hydroxy-5-(2-(methylthio)ethyl)-3,6,9-trioxo-8-((tritylthio)methyl)-2-oxa-4,7,10-triazatetradecan-14-oate
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor

  摘要：

  Three diastereomers of burkholdac B were prepared by total synthesis, enabling the full stereochemical assignment of the natural product. It is proposed that burkholdac B is identical to thailandepsin A independently isolated by Cheng from the same strain of Burkholderia thailandensis. Burkholdac B is the most potent among depsipeptide histone deacetylase inhibitors in growth inhibition of the MCF7 breast cancer cell line with an IC50 of 60 pM.

  DOI：

  10.1021/ol202197q
• 作为产物：
  描述：

  BOC-L-异亮氨酸 在 4-二甲氨基吡啶 、 正丁基锂 、 钾硼氢 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 allyl 4(S)-[(tert-butoxycarbonyl)-amino]-3(R)-hydroxy-5-methylheptanoate
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor

  摘要：

  Three diastereomers of burkholdac B were prepared by total synthesis, enabling the full stereochemical assignment of the natural product. It is proposed that burkholdac B is identical to thailandepsin A independently isolated by Cheng from the same strain of Burkholderia thailandensis. Burkholdac B is the most potent among depsipeptide histone deacetylase inhibitors in growth inhibition of the MCF7 breast cancer cell line with an IC50 of 60 pM.

  DOI：

  10.1021/ol202197q

文献信息

• A Simple Microscale Method for Determining the Relative Stereochemistry of Statine Units
  作者：Alejandro Preciado、Philip G. Williams

  DOI：10.1021/jo8012429

  日期：2008.12.5

  A simple method to determine the relative stereochemistry of statine amino acids (gamma-amino-beta-hydroxyacids) by using (1)H NMR spectroscopy is described. Configurational assignment of statine units within complex natural products is possible without degradation or derivatization as the syn and anti diastereomers can be distinguished by using a combination of chemical shift and coupling constant

  描述了一种通过使用（1）H NMR光谱确定他汀类氨基酸（γ-氨基-β-羟基酸）的相对立体化学的简单方法。在复杂的天然产物中，他汀类单元的构型分配是可能的，而不会降解或衍生化，因为可以通过结合使用化学位移和衍生自α-亚甲基ABX系统的耦合常数信息来区分顺式和反非对映异构体。提供了七个示例，说明了该方法的范围和局限性。这些示例的复杂性范围很广，从简单的他汀类药物单元到环状二肽肽，如坦丹林B。
• Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor
  作者：Hanae Benelkebir、Alison M. Donlevy、Graham Packham、A. Ganesan

  DOI：10.1021/ol202197q

  日期：2011.12.16

  Three diastereomers of burkholdac B were prepared by total synthesis, enabling the full stereochemical assignment of the natural product. It is proposed that burkholdac B is identical to thailandepsin A independently isolated by Cheng from the same strain of Burkholderia thailandensis. Burkholdac B is the most potent among depsipeptide histone deacetylase inhibitors in growth inhibition of the MCF7 breast cancer cell line with an IC50 of 60 pM.