ethyl (3S,4S,5S)-4-amino-3-hydroxy-5-methylheptanoate | 114715-81-0

• 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: ethyl (3S,4S,5S)-4-amino-3-hydroxy-5-methylheptanoate
• CAS: 114715-81-0
• 化学式: C₁₀H₂₁NO₃
• 分子量: 203.282
• InChiKey: DEZFPHIPSPUOQN-NRPADANISA-N

物化性质

• 沸点：
  311.3±27.0 °C(predicted)
• 密度：
  1.019±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (3S,4S,5S)-4-amino-3-hydroxy-5-methylheptanoate 在 吡啶 、 三乙胺 作用下， 反应 24.0h， 生成 [(2S,3S)-2-[(2S)-butan-2-yl]-5-oxopyrrolidin-3-yl] acetate
  参考文献：
  名称：

  Synthesis and properties of the eight isostatine stereoisomers

  摘要：

  The eight possible stereoisomers of isostatine, (3S,4R,5S)-4-amino-3-hydroxy-5-methylheptanoic acid, have been synthesized from the four isomeric D- and L-isoleucinals and D- and L-allo-isoleucinals and ethyl lithioacetate. The eight isomers have been compared for the GC retention times of their bis(trifluoroacetyl) methyl ester derivatives and the H-1 NMR properties of the gamma-lactams derived from them. The natural isomer was shown to be the 3S,4R,5S isomer.

  DOI：

  10.1021/jo00037a012
• 作为产物：
  描述：

  N-Boc-L-异亮氨醇 在 吡啶 、 chromium(VI) oxide 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 2.42h， 生成 ethyl (3S,4S,5S)-4-amino-3-hydroxy-5-methylheptanoate
  参考文献：
  名称：

  Synthesis and properties of the eight isostatine stereoisomers

  摘要：

  The eight possible stereoisomers of isostatine, (3S,4R,5S)-4-amino-3-hydroxy-5-methylheptanoic acid, have been synthesized from the four isomeric D- and L-isoleucinals and D- and L-allo-isoleucinals and ethyl lithioacetate. The eight isomers have been compared for the GC retention times of their bis(trifluoroacetyl) methyl ester derivatives and the H-1 NMR properties of the gamma-lactams derived from them. The natural isomer was shown to be the 3S,4R,5S isomer.

  DOI：

  10.1021/jo00037a012

文献信息

• Stereoselective synthesis of dolastatin 10 and its congeners
  作者：Takayuki Shioiri、Kyoko Hayashi、Yasumasa Hamada

  DOI：10.1016/s0040-4020(01)80547-0

  日期：1993.2

  Efficient synthesis of dolastatin 10 (1), a potent antitumor peptide from a sea hare Dolabella auricularia, has been achieved in a stereoselective manner. Trisnordolastatin 10 (2) and its C9-epimer (3) have also been synthesized.

  有效合成dolastatin 10（1），一种来自海兔Dolabella auricularia的有效抗肿瘤肽，以立体选择性方式实现。Trisnordolastatin 10（2）及其C 9-受体（3）也已合成。
• RINEHART, KENNETH L.;KISHORE, VIMAL;BIBLE, KEITH C.;SAKAI, RYUICHI;SULLIN+, J. NATUR. PROD., 51,(1988) N 1, 1-21
  作者：RINEHART, KENNETH L.、KISHORE, VIMAL、BIBLE, KEITH C.、SAKAI, RYUICHI、SULLIN+

  DOI：——

  日期：——