benzyl (3S,4R,5S)-3-hydroxy-5-methyl-4-[(2,2,2-trifluoroacetyl)amino]hept-6-enoate | 318974-80-0

• 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: benzyl (3S,4R,5S)-3-hydroxy-5-methyl-4-[(2,2,2-trifluoroacetyl)amino]hept-6-enoate
• CAS: 318974-80-0
• 化学式: C₁₇H₂₀F₃NO₄
• 分子量: 359.345
• InChiKey: JNQGIWOWXCXOMC-CORIIIEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (3S,4R,5S)-3-hydroxy-5-methyl-4-[(2,2,2-trifluoroacetyl)amino]hept-6-enoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到(3S,4R,5S)-3-hydroxy-5-methyl-4-[(2,2,2-trifluoroacetyl)amino]heptanoic acid
  参考文献：
  名称：

  A straightforward synthesis of protected isostatine from achiral precursors using the asymmetric chelate Claisen rearrangement

  摘要：

  Starting from achiral TFA-protected glycine crotyl ester (3) the interesting, suitable protected, enantiomerically pure beta-hydroxy-gamma-amino acid isostatine (7) was synthesized in only four steps. The amino acid obtained can directly be introduced into peptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02486-1
• 作为产物：
  描述：

  (2E)-but-2-en-1-yl N-(2,2,2-trifluoroacetyl)glycinate 在 sodium tetrahydroborate 、 magnesium ethylate 、 N,N'-羰基二咪唑 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 、 奎宁 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.16h， 生成 benzyl (3S,4R,5S)-3-hydroxy-5-methyl-4-[(2,2,2-trifluoroacetyl)amino]hept-6-enoate
  参考文献：
  名称：

  A straightforward synthesis of protected isostatine from achiral precursors using the asymmetric chelate Claisen rearrangement

  摘要：

  Starting from achiral TFA-protected glycine crotyl ester (3) the interesting, suitable protected, enantiomerically pure beta-hydroxy-gamma-amino acid isostatine (7) was synthesized in only four steps. The amino acid obtained can directly be introduced into peptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02486-1

文献信息

• A straightforward synthesis of protected isostatine from achiral precursors using the asymmetric chelate Claisen rearrangement
  作者：Uli Kazmaier、Achim Krebs

  DOI：10.1016/s0040-4039(98)02486-1

  日期：1999.1

  Starting from achiral TFA-protected glycine crotyl ester (3) the interesting, suitable protected, enantiomerically pure beta-hydroxy-gamma-amino acid isostatine (7) was synthesized in only four steps. The amino acid obtained can directly be introduced into peptides. (C) 1998 Elsevier Science Ltd. All rights reserved.