[(2S,3S)-1-chloro-4-methyl-1-oxo-2-(2,2,2-trichloroethoxycarbonylamino)pentan-3-yl] (2R,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoate | 201666-94-6

• 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: [(2S,3S)-1-chloro-4-methyl-1-oxo-2-(2,2,2-trichloroethoxycarbonylamino)pentan-3-yl] (2R,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoate
• CAS: 201666-94-6
• 化学式: C₂₅H₃₄Cl₄N₂O₈
• 分子量: 632.366
• InChiKey: BPEPMTCUTWSRGH-NQYYFHDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-1-chloro-4-methyl-1-oxo-2-(2,2,2-trichloroethoxycarbonylamino)pentan-3-yl] (2R,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoate 、 (S)-2-[(R)-2-({(S)-2-[Benzyloxy-((R)-1-benzyloxycarbonyl-hexahydro-pyridazine-3-carbonyl)-amino]-propionyl}-methyl-amino)-4-methyl-pentanoyl]-3-(N'-tert-butoxycarbonyl-hydrazinocarbonyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester 在 silver cyanide 作用下， 以 苯 为溶剂， 反应 0.07h， 以65%的产率得到benzyl (3S)-2-[(2R)-4-methyl-2-[methyl-[(2S)-2-[[(3R)-2-[(2S,3S)-4-methyl-3-[(2R,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoyl]oxy-2-(2,2,2-trichloroethoxycarbonylamino)pentanoyl]-1-phenylmethoxycarbonyldiazinane-3-carbonyl]-phenylmethoxyamino]propanoyl]amino]pentanoyl]-3-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]diazinane-1-carboxylate
  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：

  (2S,3S)-2-氨基-3-羟基-4-甲基-戊酸 在 四(三苯基膦)钯 吗啉 、 4-二甲氨基吡啶 、 sodium hydroxide 、 草酰氯 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.5h， 生成 [(2S,3S)-1-chloro-4-methyl-1-oxo-2-(2,2,2-trichloroethoxycarbonylamino)pentan-3-yl] (2R,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoate
  参考文献：
  名称：

  Asymmetric total synthesis of antitumour antibiotic A83586C

  摘要：

  首次完成了抗肿瘤抗生素 A83586C 的不对称全合成。

  DOI：

  10.1039/a706206k

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).
• Asymmetric total synthesis of antitumour antibiotic A83586C
  作者：Karl J. Hale、Jiaqiang Cai

  DOI：10.1039/a706206k

  日期：——

  The first asymmetric total synthesis of antitumour antibiotic A83586C has been accomplished.

  首次完成了抗肿瘤抗生素 A83586C 的不对称全合成。
• 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.