Cbz-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr(oxaz)-OMe | 184296-05-7

• 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: Cbz-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr(oxaz)-OMe
• 英文别名: methyl (4S,5R)-2-[(2S)-1-[(2S)-2-[[(2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(2R)-2-[[(2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]pyrrolidin-2-yl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 184296-05-7
• 化学式: C₅₉H₈₇N₇O₁₂Si₂
• 分子量: 1142.55
• InChiKey: DRZCDMBDLIBDKX-QDRBNDHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  80.0
• 可旋转键数：
  25.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  241.39
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Cbz-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr(oxaz)-OMe 在 palladium dihydroxide sodium hydroxide 、 五氟苯基二苯基磷酸酯 、 四丁基氟化铵 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 108.25h， 生成 (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.02,6]hexacos-1(26)-ene-7,10,13,16,19,22-hexaone
  参考文献：
  名称：

  Total Synthesis and Assignment of Configuration of Lissoclinamide 7

  摘要：

  The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline --> thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.

  DOI：

  10.1021/ja962859f
• 作为产物：
  描述：

  (2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester 在 palladium on activated charcoal 伯吉斯试剂 、 五氟苯基二苯基磷酸酯 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 Cbz-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr(oxaz)-OMe
  参考文献：
  名称：

  Total Synthesis and Assignment of Configuration of Lissoclinamide 7

  摘要：

  The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline --> thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.

  DOI：

  10.1021/ja962859f