N-Boc-4-(tributylstannyl)-L-phenylalanyl-glycylglycyl-L-phenylalanyl-L-leucine methyl ester | 1227828-36-5

• 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: N-Boc-4-(tributylstannyl)-L-phenylalanyl-glycylglycyl-L-phenylalanyl-L-leucine methyl ester
• 英文别名: methyl (2S)-4-methyl-2-[[(2S)-2-[[2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-tributylstannylphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]pentanoate
• CAS: 1227828-36-5
• 化学式: C₄₆H₇₃N₅O₈Sn
• 分子量: 942.824
• InChiKey: OWNSHHQAOWZFFU-GNTGDABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  60
• 可旋转键数：
  29
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-Boc-4-(tributylstannyl)-L-phenylalanyl-glycylglycyl-L-phenylalanyl-L-leucine methyl ester 在 三氟甲磺酸钠 、 碳酸氢钠 、 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) 、 silver(l) oxide 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以83%的产率得到4-(fluoro)-leu-enkephalin
  参考文献：
  名称：

  Silver-Catalyzed Late-Stage Fluorination

  摘要：

  Carbon-fluorine bond formation by transition metal catalysis is difficult, and only a few methods for the synthesis of aryl fluorides have been developed. All reported transition-metal-catalyzed fluorination reactions for the synthesis of functionalized arenes are based on palladium. Here we present silver catalysis for carbon-fluorine bond formation. Our report is the first example of the use of the transition metal silver to form carbon-heteroatom bonds by cross-coupling catalysis. The functional group tolerance and substrate scope presented here have not been demonstrated for any other fluorination reaction to date.

  DOI：

  10.1021/ja105834t
• 作为产物：
  描述：

  N-boc-4-(tributylstannyl)-L-phenylalanine 、 Boc-Gly-Gly-L-Phe-L-Leu-OMe 在 三氟乙酸 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 15.0h， 以72%的产率得到N-Boc-4-(tributylstannyl)-L-phenylalanyl-glycylglycyl-L-phenylalanyl-L-leucine methyl ester
  参考文献：
  名称：

  [EN] FLUORINATION OF ORGANIC COMPOUNDS
  [FR] FLUORATION DE COMPOSÉS ORGANIQUES

  摘要：

  公开号：

  WO2010059943A3

文献信息

• [EN] FLUORINATION OF ORGANIC COMPOUNDS<br/>[FR] FLUORATION DE COMPOSÉS ORGANIQUES
  申请人：HARVARD COLLEGE

  公开号：WO2010059943A3

  公开（公告）日：2010-09-10
• Silver-Catalyzed Late-Stage Fluorination
  作者：Pingping Tang、Takeru Furuya、Tobias Ritter

  DOI：10.1021/ja105834t

  日期：2010.9.1

  Carbon-fluorine bond formation by transition metal catalysis is difficult, and only a few methods for the synthesis of aryl fluorides have been developed. All reported transition-metal-catalyzed fluorination reactions for the synthesis of functionalized arenes are based on palladium. Here we present silver catalysis for carbon-fluorine bond formation. Our report is the first example of the use of the transition metal silver to form carbon-heteroatom bonds by cross-coupling catalysis. The functional group tolerance and substrate scope presented here have not been demonstrated for any other fluorination reaction to date.