(3R,4S,5S)-Boc-isostatine methyl ester | 141394-85-6

• 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: (3R,4S,5S)-Boc-isostatine methyl ester
• 英文别名: tert-butyl (2R,3S,4S)-1-(methoxycarbonyl)-2-hydroxy-4-methylhexan-3-ylcarbamate；methyl (3R,4S,5S)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoate
• CAS: 141394-85-6
• 化学式: C₁₄H₂₇NO₅
• 分子量: 289.372
• InChiKey: AGWAPTIQNSJWGW-UMNHJUIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-Boc-isostatine methyl ester 、 三氟乙酸酐 在 三氟乙酸 作用下， 反应 0.08h， 生成 (3R,4S,5S)-N,O-bis(trifluoroacetyl)isostatine methyl ester
  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

• Synthesis and properties of the eight isostatine stereoisomers
  作者：Kenneth L. Rinehart、Ryuichi Sakai、Vimal Kishore、David W. Sullins、Kai Ming Li

  DOI：10.1021/jo00037a012

  日期：1992.5

  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.