methyl (2S)-6-((2R,3R)-3-methyl-4,4-dihydro-2H-pyrrole-2-carboxamido)-2-(2,2,2-trifluoroacetamido)hexanoate | 852821-02-4

• 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: methyl (2S)-6-((2R,3R)-3-methyl-4,4-dihydro-2H-pyrrole-2-carboxamido)-2-(2,2,2-trifluoroacetamido)hexanoate
• 英文别名: Tfa-Pyl-OMe；methyl (2S)-6-[[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrole-2-carbonyl]amino]-2-[(2,2,2-trifluoroacetyl)amino]hexanoate
• CAS: 852821-02-4
• 化学式: C₁₅H₂₂F₃N₃O₄
• 分子量: 365.353
• InChiKey: JRVSMDZDFSHYEW-OUAUKWLOSA-N

物化性质

• 沸点：
  539.2±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S)-6-((2R,3R)-3-methyl-4,4-dihydro-2H-pyrrole-2-carboxamido)-2-(2,2,2-trifluoroacetamido)hexanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 18.0h， 以98%的产率得到L-pyrrolysine lithium salt
  参考文献：
  名称：

  An Asymmetric Synthesis of l-Pyrrolysine

  摘要：

  An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.

  DOI：

  10.1021/ol300045c
• 作为产物：
  描述：

  (3R,4R)-5-(tert-butoxy)-4-((tert-butoxycarbonyl)amino)-3-methyl-5-oxopentanoic acid 在 N-乙基吗啉 、 咪唑 、 三乙基硅烷 、 草酰氯 、 triflic azide 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.66h， 生成 methyl (2S)-6-((2R,3R)-3-methyl-4,4-dihydro-2H-pyrrole-2-carboxamido)-2-(2,2,2-trifluoroacetamido)hexanoate
  参考文献：
  名称：

  An Asymmetric Synthesis of l-Pyrrolysine

  摘要：

  An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.

  DOI：

  10.1021/ol300045c

文献信息

• An Asymmetric Synthesis of <scp>l</scp>-Pyrrolysine
  作者：Margaret L. Wong、Ilia A. Guzei、Laura L. Kiessling

  DOI：10.1021/ol300045c

  日期：2012.3.16

  An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.
• A Concise Synthesis of<scp>L</scp>-Pyrrolysine
  作者：Man-Yi Han、Huai-Zhen Wang、Wan-Kai An、Ju-Ying Jia、Bao-Chun Ma、Yuan Zhang、Wei Wang

  DOI：10.1002/chem.201300403

  日期：2013.6.17

  Organocatalysis: A concise synthesis of L-pyrrolysine has been accomplished in six steps from simple starting materials. The facile synthetic strategy relies on an organocatalytic Michael addition, an efficient amide coupling, and a challenging method for the imine-bond construction.