(E)-(S)-2-Dibenzylamino-6-methoxy-hex-5-enoic acid benzyl ester | 874384-03-9

• 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: (E)-(S)-2-Dibenzylamino-6-methoxy-hex-5-enoic acid benzyl ester
• CAS: 874384-03-9
• 化学式: C₂₈H₃₁NO₃
• 分子量: 429.559
• InChiKey: BOOBTHFDYBNMCQ-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  32.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-(S)-2-Dibenzylamino-6-methoxy-hex-5-enoic acid benzyl ester 在 palladium dihydroxide 盐酸 、 三异丙基硅烷 、 水 、 氢气 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium chloride 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 4.0~20.0 ℃ 、607.95 kPa 条件下， 反应 86.66h， 生成 环[2-甲基丙氨酰基-L-苯丙氨酰基-D-脯氨酰基-(2S,9R)-2-氨基-9-羟基-8-氧代癸酰基]
  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：

  dibenzyl N,N-dibenzyl-L-glutamate 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 (E)-(S)-2-Dibenzylamino-6-methoxy-hex-5-enoic 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

文献信息

• Total Synthesis, NMR Solution Structure, and Binding Model of the Potent Histone Deacetylase Inhibitor FR235222
  作者：Manuela Rodriquez、Stefania Terracciano、Elena Cini、Giulia Settembrini、Ines Bruno、Giuseppe Bifulco、Maurizio Taddei、Luigi Gomez-Paloma

  DOI：10.1002/anie.200501995

  日期：2006.1.9