methyl (6S,9S,12S,15S,18S,21S)-6-((R)-3-(benzoyloxy)-2-methylpropyl)-18-isobutyl-15-isopropyl-12-((R)-methoxy(phenyl)methyl)-2,2,5,9,17-pentamethyl-21-((R)-4-methylpent-3-en-2-yl)-4,7,10,13,16,19-hexaoxo-3-oxa-5,8,11,14,17,20-hexaazadocosan-22-oate | 855315-48-9

• 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: methyl (6S,9S,12S,15S,18S,21S)-6-((R)-3-(benzoyloxy)-2-methylpropyl)-18-isobutyl-15-isopropyl-12-((R)-methoxy(phenyl)methyl)-2,2,5,9,17-pentamethyl-21-((R)-4-methylpent-3-en-2-yl)-4,7,10,13,16,19-hexaoxo-3-oxa-5,8,11,14,17,20-hexaazadocosan-22-oate
• CAS: 855315-48-9
• 化学式: C₅₃H₈₀N₆O₁₂
• 分子量: 993.251
• InChiKey: WWIOEHNNBZXOQZ-YWLWYIGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  71.0
• 可旋转键数：
  25.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  228.08
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (6S,9S,12S,15S,18S,21S)-6-((R)-3-(benzoyloxy)-2-methylpropyl)-18-isobutyl-15-isopropyl-12-((R)-methoxy(phenyl)methyl)-2,2,5,9,17-pentamethyl-21-((R)-4-methylpent-3-en-2-yl)-4,7,10,13,16,19-hexaoxo-3-oxa-5,8,11,14,17,20-hexaazadocosan-22-oate 在 三氟乙酸 作用下， 生成 benzoic acid 4-{1-[2-methoxy-1-(1-{[1-(1-methoxycarbonyl-2,4-dimethyl-pent-3-enylcarbamoyl)-3-methyl-butyl]-methyl-carbamoyl}-2-methyl-propylcarbamoyl)-2-phenyl-ethylcarbamoyl]-ethylcarbamoyl}-2-methyl-4-methylamino-butyl 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)-N-(tert-butyloxycarbonyl)-3-methoxyphenylalanine methyl ester 在 lithium hydroxide 、 1-羟基苯并三唑一水物 、 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 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 methyl (6S,9S,12S,15S,18S,21S)-6-((R)-3-(benzoyloxy)-2-methylpropyl)-18-isobutyl-15-isopropyl-12-((R)-methoxy(phenyl)methyl)-2,2,5,9,17-pentamethyl-21-((R)-4-methylpent-3-en-2-yl)-4,7,10,13,16,19-hexaoxo-3-oxa-5,8,11,14,17,20-hexaazadocosan-22-oate
  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