(4R,5S)-3-[(2R,3S)-(3-hydroxy-2-methylnonanoyl)]-4-methyl-5-phenyloxazolidin-2-one | 694527-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-3-[(2R,3S)-(3-hydroxy-2-methylnonanoyl)]-4-methyl-5-phenyloxazolidin-2-one
• CAS: 694527-60-1
• 化学式: C₂₀H₂₉NO₄
• 分子量: 347.455
• InChiKey: FKWUTBNYKQEGBB-XYVMCAHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-[(2R,3S)-(3-hydroxy-2-methylnonanoyl)]-4-methyl-5-phenyloxazolidin-2-one 在 四(三苯基膦)钯 吗啉 、 4-二甲氨基吡啶 、 lithium hydroxide 、 氰基磷酸二乙酯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 双氧水 、 溶剂黄146 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3S)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.055
• 作为产物：
  描述：

  庚醛 、 (4R,5S)-3-丙酰基-4-甲基-5-苯基-2-噁唑烷酮 在 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.83h， 以93%的产率得到(4R,5S)-3-[(2R,3S)-(3-hydroxy-2-methylnonanoyl)]-4-methyl-5-phenyloxazolidin-2-one
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.055