(2S,9S,E)-2-(dibenzylamino)-9-(tert-butyldimethylsilyloxy)-8-oxo-6-decenoic acid benzyl ester | 874384-07-3

• 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,9S,E)-2-(dibenzylamino)-9-(tert-butyldimethylsilyloxy)-8-oxo-6-decenoic acid benzyl ester
• 英文别名: benzyl (E,2S,9S)-9-[tert-butyl(dimethyl)silyl]oxy-2-(dibenzylamino)-8-oxodec-6-enoate
• CAS: 874384-07-3
• 化学式: C₃₇H₄₉NO₄Si
• 分子量: 599.886
• InChiKey: LYZOISTZCVITEN-WCRGVSKBSA-N

物化性质

• 沸点：
  648.0±55.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.51
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,9S,E)-2-(dibenzylamino)-9-(tert-butyldimethylsilyloxy)-8-oxo-6-decenoic acid benzyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、607.95 kPa 条件下， 反应 12.0h， 以75%的产率得到(2S,9S)-2-amino-9-(tert-butyldimethylsilyloxy)-8-oxodecanoic acid
  参考文献：
  名称：

  Synthesis of 2-Amino-8-oxodecanoic Acids (Aodas) Present in Natural Hystone Deacetylase Inhibitors

  摘要：

  Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.

  DOI：

  10.1021/jo0518250
• 作为产物：
  描述：

  (S)-(-)-2-氨基-4-戊烯酸 在 三(三苯基膦)羰基氢化铑 sodium hydroxide 、 氢气 、 sodium carbonate 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium chloride 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 20.0~40.0 ℃ 、2.03 MPa 条件下， 反应 169.25h， 生成 (2S,9S,E)-2-(dibenzylamino)-9-(tert-butyldimethylsilyloxy)-8-oxo-6-decenoic acid benzyl ester
  参考文献：
  名称：

  Synthesis of 2-Amino-8-oxodecanoic Acids (Aodas) Present in Natural Hystone Deacetylase Inhibitors

  摘要：

  Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.

  DOI：

  10.1021/jo0518250