methyl (2S)-3-(2-methylbut-3-en-2-yloxy)-2-[[(2S,3R)-3-(2-methylbut-3-en-2-yloxy)-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoate | 245115-66-6

• 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: methyl (2S)-3-(2-methylbut-3-en-2-yloxy)-2-[[(2S,3R)-3-(2-methylbut-3-en-2-yloxy)-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoate
• CAS: 245115-66-6
• 化学式: C₂₆H₃₈N₂O₇
• 分子量: 490.597
• InChiKey: DESBVJCMGQQBIV-GIVPXCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-(2-methylbut-3-en-2-yloxy)-2-[[(2S,3R)-3-(2-methylbut-3-en-2-yloxy)-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoate 在 三乙基硅烷 、 palladium diacetate 、 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 methyl (2S,3S)-2-[[(2S)-2-[[(2S,3R)-2-amino-3-(2-methylbut-3-en-2-yloxy)butanoyl]amino]-3-(2-methylbut-3-en-2-yloxy)propanoyl]amino]-3-methylpentanoate
  参考文献：
  名称：

  Total synthesis of the putative structure of the marine metabolite trunkamide A

  摘要：

  The structure assigned to trunkamide A, a cycloheptapeptide alkaloid isolated from the colonial ascidian Lissoclinum sp., was prepared via segment condensations and an efficient oxazoline-thiazoline interconversion. The novel reverse prenylated serine and threonine amino acid building blocks were obtained by Lewis acid assisted opening of aziridines. In light of this total synthesis, the structure of natural trunkamide A needs to be revised. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00957-0
• 作为产物：
  描述：

  (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester 在 lithium hydroxide 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 methyl (2S)-3-(2-methylbut-3-en-2-yloxy)-2-[[(2S,3R)-3-(2-methylbut-3-en-2-yloxy)-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoate
  参考文献：
  名称：

  Total synthesis of the putative structure of the marine metabolite trunkamide A

  摘要：

  The structure assigned to trunkamide A, a cycloheptapeptide alkaloid isolated from the colonial ascidian Lissoclinum sp., was prepared via segment condensations and an efficient oxazoline-thiazoline interconversion. The novel reverse prenylated serine and threonine amino acid building blocks were obtained by Lewis acid assisted opening of aziridines. In light of this total synthesis, the structure of natural trunkamide A needs to be revised. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00957-0

文献信息

• Total synthesis of the putative structure of the marine metabolite trunkamide A
  作者：Peter Wipf、Yoshikazu Uto

  DOI：10.1016/s0040-4039(99)00957-0

  日期：1999.7

  The structure assigned to trunkamide A, a cycloheptapeptide alkaloid isolated from the colonial ascidian Lissoclinum sp., was prepared via segment condensations and an efficient oxazoline-thiazoline interconversion. The novel reverse prenylated serine and threonine amino acid building blocks were obtained by Lewis acid assisted opening of aziridines. In light of this total synthesis, the structure of natural trunkamide A needs to be revised. (C) 1999 Elsevier Science Ltd. All rights reserved.