(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid | 753487-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
• 英文别名: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[1-(2-methylbut-3-en-2-yl)indol-3-yl]propanoic acid
• CAS: 753487-61-5
• 化学式: C₃₇H₄₄N₂O₅Si
• 分子量: 624.852
• InChiKey: MALNUYXPSUAMNB-JHOUSYSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.62
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 在 哌啶 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (R)-3-((2S,5S)-5-{(R)-(tert-butyl-dimethyl-silanyloxy)-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-methyl}-1-methyl-3,6-dioxo-piperazin-2-yl)-2-methyl-propyl ester
  参考文献：
  名称：

  Macrocyclization studies and total synthesis of cyclomarin C, an anti-inflammatory marine cyclopeptide

  摘要：

  The studies on macrocyclization at possible sites toward the total synthesis of cyclomarin C are described. The results showed that both Trp and Phe derivatives involved in the target could not be the terminals of the final linear peptide precursors. Additionally, preparation of corresponding dipeptides with an N-methyl amide bond is not favorable in the synthesis of linear precursors. Site d was finally proved a proper site for the cyclopeptide formation, and the corresponding head-to-tail macrocyclization was achieved under mild conditions and gave repeatable and satisfactory yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.058
• 作为产物：
  描述：

  (2S,3R)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester 在 palladium diacetate 三乙基硅烷 、 lithium hydroxide 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 68.0h， 生成 (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n

文献信息

• Total Synthesis of Cyclomarin C
  作者：Shi-Jun Wen、Zhu-Jun Yao

  DOI：10.1021/ol049065n

  日期：2004.8.1

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.
• Macrocyclization studies and total synthesis of cyclomarin C, an anti-inflammatory marine cyclopeptide
  作者：Shi-Jun Wen、Tai-Shan Hu、Zhu-Jun Yao

  DOI：10.1016/j.tet.2005.03.058

  日期：2005.5

  The studies on macrocyclization at possible sites toward the total synthesis of cyclomarin C are described. The results showed that both Trp and Phe derivatives involved in the target could not be the terminals of the final linear peptide precursors. Additionally, preparation of corresponding dipeptides with an N-methyl amide bond is not favorable in the synthesis of linear precursors. Site d was finally proved a proper site for the cyclopeptide formation, and the corresponding head-to-tail macrocyclization was achieved under mild conditions and gave repeatable and satisfactory yields. (c) 2005 Elsevier Ltd. All rights reserved.