(3S,4R,5R)-allyl 4-(tert-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate | 1351107-13-5

• 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: (3S,4R,5R)-allyl 4-(tert-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate
• 英文别名: prop-2-enyl (3S,4R,5R)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoate
• CAS: 1351107-13-5
• 化学式: C₁₆H₂₉NO₅
• 分子量: 315.41
• InChiKey: DMFDBQKOIUXBHH-MBNYWOFBSA-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：

  (3S,4R,5R)-allyl 4-(tert-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 (3S,4R,5R)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-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
• 作为产物：
  描述：

  Boc-D-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 (3S,4R,5R)-allyl 4-(tert-butoxycarbonylamino)-3-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