(3S)-N(1)-Z-piperazic acid t-butylhydrazide | 439292-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S)-N(1)-Z-piperazic acid t-butylhydrazide
• 英文别名: benzyl (3S)-3-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]diazinane-1-carboxylate
• CAS: 439292-93-0
• 化学式: C₁₈H₂₆N₄O₅
• 分子量: 378.428
• InChiKey: DQESFIAAUZYROS-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-N(1)-Z-piperazic acid t-butylhydrazide 在 2,3,5-三甲基吡啶 、 silver cyanide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 二乙胺 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 17.41h， 生成 1-O-benzyl 2-O-(9H-fluoren-9-ylmethyl) (3R)-3-[[(2S)-1-[methyl-[(2R)-4-methyl-1-[(6S)-6-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]-2-phenylmethoxycarbonyldiazinan-1-yl]-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]-phenylmethoxycarbamoyl]diazinane-1,2-dicarboxylate
  参考文献：
  名称：

  Synthetic Route to the GE3 Cyclodepsipeptide

  摘要：

  [GRAPHICS]A reasonably efficient [2 + 2 + 2] fragment condensation strategy has been developed for assembling the cyclodepsipeptide sector of GE3 that involves 5-7. A Carpino HATU-mediated macrolactamization was used to close the 19-membered cyclodepsipeptide ring.

  DOI：

  10.1021/ol025895u
• 作为产物：
  描述：

  (3S)-2-(9H-fluoren-9-ylmethoxycarbonyl)-1-phenylmethoxycarbonyldiazinane-3-carboxylic acid 在 二乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 21.25h， 生成 (3S)-N(1)-Z-piperazic acid t-butylhydrazide
  参考文献：
  名称：

  Synthetic Route to the GE3 Cyclodepsipeptide

  摘要：

  [GRAPHICS]A reasonably efficient [2 + 2 + 2] fragment condensation strategy has been developed for assembling the cyclodepsipeptide sector of GE3 that involves 5-7. A Carpino HATU-mediated macrolactamization was used to close the 19-membered cyclodepsipeptide ring.

  DOI：

  10.1021/ol025895u

文献信息

• Total Synthesis of (+)-Azinothricin and (+)-Kettapeptin
  作者：Karl J. Hale、Soraya Manaviazar、Jonathan H. George、Marcus A. Walters、Stephen M. Dalby

  DOI：10.1021/ol802817t

  日期：2009.2.5

  Asymmetric total syntheses of (+)-azinothricin and (+)-kettapeptin have been completed through a common new pathway that exploits a highly chemoselective coupling reaction between the fully elaborated cyclodepsipeptide 5 and the glycal activated esters 3 and 4 at the final stages of both respective syntheses.
• Synthesis of A83586C Analogs with Potent Anticancer and β-Catenin/ TCF4/Osteopontin Inhibitory Effects and Insights Into How A83586C Modulates E2Fs and pRb
  作者：Karl J. Hale、Soraya Manaviazar、Linos Lazarides、Jonathan George、Marcus A. Walters、Jiaqiang Cai、Vern M. Delisser、Gurpreet S. Bhatia、S. Andrew Peak、Stephen M. Dalby、Amandine Lefranc、Ying-Nan P. Chen、Alexander W. Wood、Paul Crowe、Pauline Erwin、Mohamed El-Tanani

  DOI：10.1021/ol802818f

  日期：2009.2.5

  The synthesis of three potent new antitumor agents is described: the A83586C-citropeptin hybrid (1), the A83586C-GE3 hybrid (2), and L-Pro-A83586C (3). Significantly, compounds 1 and 2 function as highly potent inhibitors of beta-catenin/TCF4 signaling within cancer cells, while simultaneously downregulating osteopontin (Opn) expression. A83586C antitumor cyclodepsipeptides also inhibit E2F-mediated transcription by downregulating E2F1 expression and inducing dephosphorylation of the oncogenic hyperphosphorylated retinoblastoma protein (pRb).
• Synthetic Route to the GE3 Cyclodepsipeptide
  作者：Karl J. Hale、Linos Lazarides

  DOI：10.1021/ol025895u

  日期：2002.5.1

  [GRAPHICS]A reasonably efficient [2 + 2 + 2] fragment condensation strategy has been developed for assembling the cyclodepsipeptide sector of GE3 that involves 5-7. A Carpino HATU-mediated macrolactamization was used to close the 19-membered cyclodepsipeptide ring.