(2S,3S)-3-hydroxy-1-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]pyrrolidine-2-carboxylic acid | 936703-21-8

• 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: (2S,3S)-3-hydroxy-1-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]pyrrolidine-2-carboxylic acid
• CAS: 936703-21-8
• 化学式: C₂₀H₂₈N₂O₇
• 分子量: 408.452
• InChiKey: KROUBSLNKLSJSV-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  、 (2S,3S)-3-hydroxy-1-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]pyrrolidine-2-carboxylic acid 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,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以0.736 g的产率得到1-O-cyclohexyl 4-O-[(3R)-1-[[(2R,3R)-1-[[(2R)-1-[(2S,3S)-2-[[(2S)-1-[[(2R,3R)-4-cyclohexyloxy-1,4-dioxo-3-phenylmethoxy-1-prop-2-enoxybutan-2-yl]amino]-5-(9H-fluoren-9-ylmethoxycarbonylamino)-1-oxopentan-2-yl]carbamoyl]-3-hydroxypyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-14-methyl-1-oxopentadecan-3-yl] (2S,3S)-3-[[(2S,3S)-3-hydroxy-1-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]pyrrolidine-2-carbonyl]amino]-2-phenylmethoxybutanedioate
  参考文献：
  名称：

  Total Synthesis of Plusbacin A₃:  A Depsipeptide Antibiotic Active Against Vancomycin-Resistant Bacteria

  摘要：

  Plusbacin A(3) is a depsipeptide antibiotic isolated from Pseudomonas sp. Although the stereochemistry at the lactone stereocenter had not been determined, biological evaluation of this compound demonstrated it to have promising antibacterial activity against vancomycin-resistant enterococci. Its mechanism of action remains to be conclusively established, but it is believed to exert its antibiotic effect through inhibition of bacterial cell wall biosynthesis. In this paper, we describe the first total synthesis of plusbacin A(3) and assign the stereochemistry for the remaining unassigned lactone stereocenter.

  DOI：

  10.1021/ja068455x
• 作为产物：
  描述：

  N-Boc-O-苄基-D-丝氨酸 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦 盐酸 、 苯硅烷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 (2S,3S)-3-hydroxy-1-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Total Synthesis of Plusbacin A₃:  A Depsipeptide Antibiotic Active Against Vancomycin-Resistant Bacteria

  摘要：

  Plusbacin A(3) is a depsipeptide antibiotic isolated from Pseudomonas sp. Although the stereochemistry at the lactone stereocenter had not been determined, biological evaluation of this compound demonstrated it to have promising antibacterial activity against vancomycin-resistant enterococci. Its mechanism of action remains to be conclusively established, but it is believed to exert its antibiotic effect through inhibition of bacterial cell wall biosynthesis. In this paper, we describe the first total synthesis of plusbacin A(3) and assign the stereochemistry for the remaining unassigned lactone stereocenter.

  DOI：

  10.1021/ja068455x

文献信息

• Total Synthesis of Plusbacin A₃:  A Depsipeptide Antibiotic Active Against Vancomycin-Resistant Bacteria
  作者：Aaron Wohlrab、Ryan Lamer、Michael S. VanNieuwenhze

  DOI：10.1021/ja068455x

  日期：2007.4.1

  Plusbacin A(3) is a depsipeptide antibiotic isolated from Pseudomonas sp. Although the stereochemistry at the lactone stereocenter had not been determined, biological evaluation of this compound demonstrated it to have promising antibacterial activity against vancomycin-resistant enterococci. Its mechanism of action remains to be conclusively established, but it is believed to exert its antibiotic effect through inhibition of bacterial cell wall biosynthesis. In this paper, we describe the first total synthesis of plusbacin A(3) and assign the stereochemistry for the remaining unassigned lactone stereocenter.