N-Cbz-Val-Leu-Ala-OH | 146847-72-5

• 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: N-Cbz-Val-Leu-Ala-OH
• 英文别名: Cbz-Val-Leu-Ala-OH；(2S)-2-[[(2S)-4-methyl-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]pentanoyl]amino]propanoic acid
• CAS: 146847-72-5
• 化学式: C₂₂H₃₃N₃O₆
• 分子量: 435.521
• InChiKey: IFMQVERKPIOUDX-SZMVWBNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Cbz-Val-Leu-Ala-OH 、 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以201 mg的产率得到(5S,8S,11S,14S)-((2'R,3'R,4'S,6'S)-1'-(2"-(benzyloxy)-2"-oxoethylamino)-2', 4',6'-trimethyl-1'-oxododecan-3'-yl) 8-isobutyl-5-isopropyl-11,14-dimethyl-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oate
  参考文献：
  名称：

  Asymmetric synthesis of emericellamide B

  摘要：

  Asymmetric total synthesis of emericellamide B (9.4%, 17 longest linear steps) is detailed in this report. In this synthetic route, the highly methylated (2R,3R,4S,6S)-3-hydroxy-2,4,6-trimethyldodecanoic acid (HTMD) unit was effectively prepared through the asymmetric methylation, Wittig and Horner-Wadsworth-Emmons reaction. Moreover, pentafluorophenyl diphenylphophinate (FDPP) proved to be an effective condensation reagent for the macrolactamization between C14 and C18. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.07.023

文献信息

• Total Synthesis of Emericellamide A: A Secondary Metabolite of Marine Cyclic Depsipeptide with Antimicrobial Properties
  作者：Bang-Guo Wei、Guo-Qiang Lin、Jing-Yi Ma、Long-Fei Xu、Wen-Feng Huang

  DOI：10.1055/s-0029-1217158

  日期：——

  Emericellamide A is a secondary metabolite of marine cyclic depsipeptide from the co-culture of the marine-derived fungus Emericella sp. and actinomycete Salinispora arenicola. A general method for the total synthesis of emericellamide A is depicted in this report.

  Emericellaamide A 是海洋源性真菌 Emericella sp. 共培养的海洋环缩肽的次级代谢产物。和放线菌 Salinispora arenicola。本报告描述了全合成 emericellaamide A 的一般方法。
• Asymmetric synthesis of emericellamide B
  作者：Rong-Guo Ren、Jing-Yi Ma、Zhuo-Ya Mao、Yi-Wen Liu、Bang-Guo Wei

  DOI：10.1016/j.cclet.2015.07.023

  日期：2015.10

  Asymmetric total synthesis of emericellamide B (9.4%, 17 longest linear steps) is detailed in this report. In this synthetic route, the highly methylated (2R,3R,4S,6S)-3-hydroxy-2,4,6-trimethyldodecanoic acid (HTMD) unit was effectively prepared through the asymmetric methylation, Wittig and Horner-Wadsworth-Emmons reaction. Moreover, pentafluorophenyl diphenylphophinate (FDPP) proved to be an effective condensation reagent for the macrolactamization between C14 and C18. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.