(3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene | 214753-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene
• CAS: 214753-16-9
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: XCHUBQQLHPVVEE-VYRBHSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.79
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene 在 palladium on activated charcoal 咪唑 、 草酰氯 、 四丁基氟化铵 、 氢气 、 双氧水 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯甲腈 为溶剂， 反应 44.0h， 生成 dihydroeponemycin-biotin
  参考文献：
  名称：

  Eponemycin analogues: syntheses and use as probes of angiogenesis

  摘要：

  Derivatives of the epoxy-beta-aminoketone containing natural product eponemycin have been prepared in order to study the molecular mode of action of this anti-angiogenic compound. Synthesis and use of a biotinylated dihydroeponemycin analogue demonstrated that dihydroeponemycin forms a covalent adduct with at least two intracellular proteins in human endothelial cells. Pretreatment of cells with a five equivalent excess of dihydroeponemycin precluded biotin-dihydroeponemycin binding indicating a specific interaction between natural product and the target proteins. This biotin-dihydroeponemycin derivative will prove useful in the purification and identification of eponemycin receptors. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00089-3
• 作为产物：
  描述：

  2-溴-2-丙烯-1-醇 、 N-carbobenzoxy-L-leucinal 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 7.5h， 以54%的产率得到(3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene
  参考文献：
  名称：

  Eponemycin analogues: syntheses and use as probes of angiogenesis

  摘要：

  Derivatives of the epoxy-beta-aminoketone containing natural product eponemycin have been prepared in order to study the molecular mode of action of this anti-angiogenic compound. Synthesis and use of a biotinylated dihydroeponemycin analogue demonstrated that dihydroeponemycin forms a covalent adduct with at least two intracellular proteins in human endothelial cells. Pretreatment of cells with a five equivalent excess of dihydroeponemycin precluded biotin-dihydroeponemycin binding indicating a specific interaction between natural product and the target proteins. This biotin-dihydroeponemycin derivative will prove useful in the purification and identification of eponemycin receptors. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00089-3