(2R,3S,4R)-4-acetoxy-5-N-(allyloxycarbonyl)amino-2,3-isopropylidenedioxypentan-1-ol | 1254754-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-4-acetoxy-5-N-(allyloxycarbonyl)amino-2,3-isopropylidenedioxypentan-1-ol
• 英文别名: [(1R)-1-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(prop-2-enoxycarbonylamino)ethyl] acetate
• CAS: 1254754-86-3
• 化学式: C₁₄H₂₃NO₇
• 分子量: 317.339
• InChiKey: HHTBQSNIXVYSQX-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-4-acetoxy-5-N-(allyloxycarbonyl)amino-2,3-isopropylidenedioxypentan-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以41 g的产率得到(3S,4S,5R)-5-acetoxy-N-allyloxycarbonyl-3,4-isopropylidenedioxypiperidin-2-one
  参考文献：
  名称：

  Synthesis and DNA cleavage evaluation of epoxypiperidine derivatives bearing a dehydroamino acid unit

  摘要：

  Epoxypiperidine derivatives bearing a dehydroamino acid unit were designed and synthesized as novel DNA alkylating agents based on the structure of azinomycins. A relaxation assay of plasmid DNA revealed that the epoxypiperidine derivative 3 has a DNA cleavage activity. Based on the studies, it would appear that the electron density of the amino group of epoxypiperidines plays a critically important role in the DNA cleavage. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.027
• 作为产物：
  描述：

  (2R,3S,4R)-4-acetoxy-5-N-(allyloxycarbonyl)amino-1-tert-butyldimethylsiloxy-2,3-isopropylidenedioxypentane 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(2R,3S,4R)-4-acetoxy-5-N-(allyloxycarbonyl)amino-2,3-isopropylidenedioxypentan-1-ol
  参考文献：
  名称：

  Synthesis and DNA cleavage evaluation of epoxypiperidine derivatives bearing a dehydroamino acid unit

  摘要：

  Epoxypiperidine derivatives bearing a dehydroamino acid unit were designed and synthesized as novel DNA alkylating agents based on the structure of azinomycins. A relaxation assay of plasmid DNA revealed that the epoxypiperidine derivative 3 has a DNA cleavage activity. Based on the studies, it would appear that the electron density of the amino group of epoxypiperidines plays a critically important role in the DNA cleavage. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.027