allyl (3S,4R,5S)-4-(t-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate | 1309766-93-5

• 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: allyl (3S,4R,5S)-4-(t-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate
• 英文别名: (3S,4R,5S)-allyl 4-(tert-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate；prop-2-enyl (3S,4R,5S)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoate
• CAS: 1309766-93-5
• 化学式: C₁₆H₂₉NO₅
• 分子量: 315.41
• InChiKey: DMFDBQKOIUXBHH-SGMGOOAPSA-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 (3S,4R,5S)-4-(t-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.0h， 生成 allyl (3S,4R,5S)-4-[(S)-2-{(R)-2-[(E)-(S)-3-hydroxy-7-(tritylthio)-4-heptenoylamino]propionylamino}-3-(tritylthio)propionylamino]-3-hydroxy-5-methylheptanoate
  参考文献：
  名称：

  Total synthesis of spiruchostatin B aided by an automated synthesizer

  摘要：

  天然产物HDAC抑制剂spirochostatin B的全合成成功实现。通过自动化合成器执行了一种包含不对称羟醛反应的5步合成路线，得到了(E)-(S)-3-羟基-7-硫-4-庚烯酸片段，这一片段是包含半胱氨酸的脱硫肽类天然产物，如spirochostatins、FK228、FR901375和largazole，它们对HDACs具有抑制活性的关键结构。

  DOI：

  10.1039/c0ob01169j
• 作为产物：
  描述：

  (4R,5S)-allyl 4-(tert-butoxycarbonylamino)-5-methyl-3-oxoheptanoate 在 钾硼氢 作用下， 以 甲醇 为溶剂， 反应 0.83h， 以69%的产率得到allyl (3S,4R,5S)-4-(t-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

文献信息

• Total synthesis of spiruchostatin B aided by an automated synthesizer
  作者：Shinichiro Fuse、Kumiko Okada、Yusuke Iijima、Asami Munakata、Kazuhiro Machida、Takashi Takahashi、Motoki Takagi、Kazuo Shin-ya、Takayuki Doi

  DOI：10.1039/c0ob01169j

  日期：——

  The total synthesis of a natural productHDAC inhibitor, spiruchostatin B, was successfully achieved. A 5-step synthesis that included an asymmetric aldol reaction was carried out in an automated synthesizer to provide an (E)-(S)-3-hydroxy-7-thio-4-heptenoic acid segment that is the crucial structure of cysteine-containing, depsipeptidic natural products such as spiruchostatins, FK228, FR901375, and largazole for their inhibitory activity against HDACs.

  天然产物HDAC抑制剂spirochostatin B的全合成成功实现。通过自动化合成器执行了一种包含不对称羟醛反应的5步合成路线，得到了(E)-(S)-3-羟基-7-硫-4-庚烯酸片段，这一片段是包含半胱氨酸的脱硫肽类天然产物，如spirochostatins、FK228、FR901375和largazole，它们对HDACs具有抑制活性的关键结构。
• 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.