(2S)-N-<4'-methylpentanoyl>bornane-10,2-sultam | 168958-05-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S)-N-<4'-methylpentanoyl>bornane-10,2-sultam
• 英文别名: (2S)-N-(4-methylpentanoyl)camphorsultam；1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-4-methylpentan-1-one
• CAS: 168958-05-2
• 化学式: C₁₆H₂₇NO₃S
• 分子量: 313.461
• InChiKey: JMRGZNPUBUMPAN-XEZPLFJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S)-N-<4'-methylpentanoyl>bornane-10,2-sultam 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 Sodium; (Z)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-4-methyl-pent-1-en-1-olate
  参考文献：
  名称：

  Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Electrophilic amination of Oppolzer's acyl sultams in the synthesis of L-[15N]alanine, L-[15N]valine, L-[15N]leucine, L-[15N]phenylalanine and L-[1-13C, 15N]valine

  摘要：

  Using 1-chloro-1-[N-15]nitrosocyclohexane, we have prepared five L-[alpha-N-15]amino acids. The stereoselective electophillic hydroxyamination of (S)-acylbornane-10,2-sultams, followed by Zn-o/H+ reduction, and alkaline cleavage of the chiral auxiliary, gave the amino acids in 97.2-99.5% e.e. By starting with labeled (S)-acylbornane-10,2-sultams this stereoselective route could be to prepare many C-13 and/or N-15 isotopomers of alpha-amino acids.

  DOI：

  10.1002/(sici)1099-1344(199603)38:3<239::aid-jlcr831>3.0.co;2-e
• 作为产物：
  描述：

  异己酰氯 、 (+)-camphorsultam 在 sodium hydride 作用下， 生成 (2S)-N-<4'-methylpentanoyl>bornane-10,2-sultam
  参考文献：
  名称：

  Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Electrophilic amination of Oppolzer's acyl sultams in the synthesis of L-[15N]alanine, L-[15N]valine, L-[15N]leucine, L-[15N]phenylalanine and L-[1-13C, 15N]valine

  摘要：

  Using 1-chloro-1-[N-15]nitrosocyclohexane, we have prepared five L-[alpha-N-15]amino acids. The stereoselective electophillic hydroxyamination of (S)-acylbornane-10,2-sultams, followed by Zn-o/H+ reduction, and alkaline cleavage of the chiral auxiliary, gave the amino acids in 97.2-99.5% e.e. By starting with labeled (S)-acylbornane-10,2-sultams this stereoselective route could be to prepare many C-13 and/or N-15 isotopomers of alpha-amino acids.

  DOI：

  10.1002/(sici)1099-1344(199603)38:3<239::aid-jlcr831>3.0.co;2-e

文献信息

• New Scalable Asymmetric Aminomethylation Reaction for the Synthesis of β2-Amino Acids
  作者：Roba Moumné、Bernard Denise、Karine Guitot、Henri Rudler、Solange Lavielle、Philippe Karoyan

  DOI：10.1002/ejoc.200600926

  日期：2007.4

  β-Amino acids are useful tools in the design of peptidomimetics, and the development of new methods for their syntheses, particularly the synthesis of β2-amino acids, remains an important challenge. Here we report a new scalable route based on the aminomethylation of silyl ketene N,O-acetals by Mannich-type iminium electrophiles. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  β-氨基酸是设计拟肽的有用工具，开发其合成的新方法，尤其是 β2-氨基酸的合成，仍然是一个重要的挑战。在这里，我们报告了一种新的可扩展路线，该路线基于 Mannich 型亚胺鎓亲电试剂对甲硅烷基乙烯酮 N,O-缩醛的氨甲基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)