(S)-2-{(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-propionic acid 2,2,2-trichloro-ethyl ester | 156706-57-9

• 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: (S)-2-{(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-propionic acid 2,2,2-trichloro-ethyl ester
• 英文别名: 2,2,2-trichloroethyl (2S)-2-[[(2R)-3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoyl]amino]propanoate
• CAS: 156706-57-9
• 化学式: C₂₆H₄₁Cl₃N₂O₆Si
• 分子量: 612.066
• InChiKey: UHUXJTRXKOMBOG-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-{(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-propionic acid 2,2,2-trichloro-ethyl ester 在 三氟甲磺酸三甲基硅酯 、 mercury(II) diacetate 、 ammonium acetate 、 碘 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 苯甲醚 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 136.0h， 生成 (2S)-2-[[(2R)-3-[4-[tert-butyl(dimethyl)silyl]oxy-3-iodophenyl]-2-[[(2S)-2-[[(E,2S,6R,8S)-8-hydroxy-2,4,6-trimethylnon-4-enoyl]amino]propanoyl]-methylamino]propanoyl]amino]propanoic acid
  参考文献：
  名称：

  An Expeditious Synthesis of Geodiamolide A, an 18-Membered Cytotoxic Depsipeptide from Marine Sponges

  摘要：

  Geodiamolide A (1) has been efficiently synthesized from the polypropionate and tripeptide units using the Evans asymmetric alkylation, the Mitsunobu esterification, and the macrolactamization with diphenyl phosphorazidate (DPPA) as key steps. Efficient esterification between the complex polyketide and tripeptide units was also realized under high pressure conditions.

  DOI：

  10.3987/com-97-s41
• 作为产物：
  描述：

  Boc-D-酪氨酸 在 咪唑 、 氰基磷酸二乙酯 、 水 、 叔丁基锂 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.5h， 生成 (S)-2-{(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-propionic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  An Expeditious Synthesis of Geodiamolide A, an 18-Membered Cytotoxic Depsipeptide from Marine Sponges

  摘要：

  Geodiamolide A (1) has been efficiently synthesized from the polypropionate and tripeptide units using the Evans asymmetric alkylation, the Mitsunobu esterification, and the macrolactamization with diphenyl phosphorazidate (DPPA) as key steps. Efficient esterification between the complex polyketide and tripeptide units was also realized under high pressure conditions.

  DOI：

  10.3987/com-97-s41

文献信息

• Efficient syntheses of geodiamolide A and jaspamide, cytotoxic and antifungal cyclic depsipeptides of marine sponge origin
  作者：Takayuki Imaeda、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4039(00)75846-1

  日期：——

  Geodiamolide A (1a) and jaspamide (2) have been efficiently synthesized by use of the Evans asymmetric alkylation, the Mitsunobu esterification, and the DPPA macrolactamization as key steps.

  通过使用Evans不对称烷基化，Mitsunobu酯化和DPPA大内酰胺化作为关键步骤，有效地合成了Geodiamolide A（1a）和jaspamide（2）。
• An Expeditious Synthesis of Geodiamolide A, an 18-Membered Cytotoxic Depsipeptide from Marine Sponges
  作者：Takayuki Shioiri、Takayuki Imaeda、Yasumasa Hamada

  DOI：10.3987/com-97-s41

  日期：——

  Geodiamolide A (1) has been efficiently synthesized from the polypropionate and tripeptide units using the Evans asymmetric alkylation, the Mitsunobu esterification, and the macrolactamization with diphenyl phosphorazidate (DPPA) as key steps. Efficient esterification between the complex polyketide and tripeptide units was also realized under high pressure conditions.