(2R,3S,4R)-5-N-benzylamino-1-tert-butyldimethylsiloxy-2,3-isopropylidenedioxypentan-4-ol | 1254754-78-3

• 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: (2R,3S,4R)-5-N-benzylamino-1-tert-butyldimethylsiloxy-2,3-isopropylidenedioxypentan-4-ol
• CAS: 1254754-78-3
• 化学式: C₂₁H₃₇NO₄Si
• 分子量: 395.615
• InChiKey: UBBCQBDTZDMXPJ-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  59.95
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-5-N-benzylamino-1-tert-butyldimethylsiloxy-2,3-isopropylidenedioxypentan-4-ol 在 20 % Pd(OH)2/C 、 甲酸铵 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以100%的产率得到(2R,3S,4R)-5-amino-1-tert-butyldimethylsiloxy-2,3-isopropylidenedioxypentan-4-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
• 作为产物：
  描述：

  (2R,3S,4R)-5-benzylamino-2,3-isopropylidenedioxypentane-1,4-diol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到(2R,3S,4R)-5-N-benzylamino-1-tert-butyldimethylsiloxy-2,3-isopropylidenedioxypentan-4-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

文献信息

• Synthesis and DNA cleavage evaluation of epoxypiperidine derivatives bearing a dehydroamino acid unit
  作者：Takao Yamaguchi、Yuji Kawada、Satoshi Obika、Takeshi Imanishi、Kazuyuki Miyashita

  DOI：10.1016/j.tet.2010.08.027

  日期：2010.10

  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.