f₄-Fmoc-OSu | 916686-38-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: f₄-Fmoc-OSu
• 英文别名: [2,7-bis(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9H-fluoren-9-yl]methyl (2,5-dioxopyrrolidin-1-yl) carbonate
• CAS: 916686-38-9
• 化学式: C₃₁H₂₁F₁₈NO₅
• 分子量: 829.483
• InChiKey: MKNRQLKPNJHHBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  f₄-Fmoc-OSu 在 sodium carbonate 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.33h， 生成 f₄-Fmoc-Ala-Thr-OBn
  参考文献：
  名称：

  Tenuecyclamide A的所有立体异构体的合成采用氟-Fmoc策略。

  摘要：

  使用d- / l-丙氨酸与由不同的f-Fmoc标签编码的每种立体异构体的混合物，可以实现Tenuecyclamide A所有立体异构体的简洁液相组合合成。已经证明使用f-Fmoc试剂作为氨基酸保护基的合成策略是用于多种多肽类似物合成的有用方法。

  DOI：

  10.1021/jo401647k
• 作为产物：
  描述：

  2,7-二硝基芴 在 sodium tetrahydroborate 、 tetrafluoroboric acid 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 N,N-二甲基苯胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 68.5h， 生成 f₄-Fmoc-OSu
  参考文献：
  名称：

  Development of efficient processes for multi-gram scale and divergent preparation of fluorous-Fmoc reagents

  摘要：

  An optimized, multi-gram scale synthesis of fluorous-Fmoc reagents is described. Fmoc reagents bearing C3F7, C4F9, and C6F13 chains were prepared on multi-gram scale (ca. 1.0-7.0 g) in eight steps with overall yields of 73%, 60%, and 90%, respectively. The order of addition of the fluorous alkenes in a one-pot double tagging Heck reaction was also investigated in order to conduct an encoded mixture synthesis of f-Fmoc reagents. The target f-Fmoc reagents bearing C3F7, C4F9, and C6F13 chains could be effectively separated based on the fluorine content of the molecules. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.083

文献信息

• Fluorous Mixture Synthesis of Tripeptides and Pentapeptides Using­ a Fluorous-Fmoc Protection Strategy
  作者：Masato Matsugi、Yuya Sugiyama、Ryuhei Shirai、Masaki Hirose、Tomoko Watanabe、Ayana Yoshida、Natsuki Endo、Toshiya Hayashi、Takayuki Shioiri

  DOI：10.1055/s-0036-1588698

  日期：——

  split-type synthesis of various tripeptides and pentapeptides was conducted using a fluorous-Fmoc protection strategy. Fluorous-Fmoc reagents were effectively used as both the protecting group for the amino function and the encoding tag for the amino acid structure. Several of the synthetic peptides prepared showed high activities in an ACE inhibitory assay. A liquid-phase split-type synthesis of various

  摘要 使用氟-Fmoc保护策略进行了各种三肽和五肽的液相分裂型合成。氟-Fmoc试剂可有效地用作氨基功能的保护基和氨基酸结构的编码标签。所制备的几种合成肽在ACE抑制试验中显示出高活性。 使用氟-Fmoc保护策略进行了各种三肽和五肽的液相分裂型合成。氟-Fmoc试剂可有效地用作氨基功能的保护基和氨基酸结构的编码标签。所制备的几种合成肽在ACE抑制试验中显示出高活性。
• Concise Synthesis of All Stereoisomers of Dendroamide A by Fluorous Mixture Synthesis Based on Fluorous-Fmoc Protection of Amino Acids
  作者：Hiroaki Takahashi、Natsuki Endo、Hitomi Takanose、Yuya Sugiyama、Fumitaka Eguchi、Kazuma Oguri、Hiromi Hamamoto、Takayuki Shioiri、Masato Matsugi

  DOI：10.1002/ejoc.201500394

  日期：2015.6

  A liquid-phase split-type synthesis of all the stereoisomers of dendroamide A, which exhibits multidrug-resistance reversing activity, has been carried out. The key to the concise synthesis was the fluorous-Fmoc protection strategy of each of the starting materials (D- and L-alanine and D- and L-valine). By using the fluorous-Fmoc encoding method, the target stereoisomers were effectively synthesized

  树酰胺 A 的所有立体异构体的液相分离型合成已进行，该立体异构体具有多药耐药逆转活性。简洁合成的关键是每种原料（D-和L-丙氨酸以及D-和L-缬氨酸）的氟-Fmoc保护策略。通过使用 fluorous-Fmoc 编码方法，目标立体异构体可以在比相应的线性合成路​​线更少的步骤中有效地单独合成。
• Liquid-Phase Split-Type Combinatorial Synthesis of Tripeptide Derivatives Encoded by Fluorous Fmoc Reagents
  作者：Masato Matsugi、Yuya Sugiyama、Masaki Hirose、Junko Matsui、Natsuki Endo、Hiromi Hamamoto、Takayuki Shioiri

  DOI：10.1055/s-0033-1339924

  日期：——

  A liquid-phase mixture synthesis of 18 tripeptides, some of which are analogues of ACE inhibitors, was effectively conducted by using fluorous Fmoc reagents as encoding tags.
• A Synthesis of All Stereoisomers of Tenuecyclamide A Employing a Fluorous-Fmoc Strategy
  作者：Yuya Sugiyama、Fumitaka Eguchi、Atsushi Miyazaki、Koichi Hayashi、Hiroaki Takahashi、Hiromi Hamamoto、Takayuki Shioiri、Masato Matsugi

  DOI：10.1021/jo401647k

  日期：2013.10.18

  A concise liquid-phase combinatorial synthesis of all stereoisomers of Tenuecyclamide A was achieved using a mixture of d-/l-alanine with each stereoisomer encoded by a different f-Fmoc tag. The synthetic strategy using f-Fmoc reagents as the protecting group for amino acids has been demonstrated to be a useful method for diverse polypeptide analogue synthesis.

  使用d- / l-丙氨酸与由不同的f-Fmoc标签编码的每种立体异构体的混合物，可以实现Tenuecyclamide A所有立体异构体的简洁液相组合合成。已经证明使用f-Fmoc试剂作为氨基酸保护基的合成策略是用于多种多肽类似物合成的有用方法。
• Development of efficient processes for multi-gram scale and divergent preparation of fluorous-Fmoc reagents
  作者：Yuya Sugiyama、Natsuki Endo、Kazuki Ishihara、Yuki Kobayashi、Hiromi Hamamoto、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tet.2015.05.083

  日期：2015.7

  An optimized, multi-gram scale synthesis of fluorous-Fmoc reagents is described. Fmoc reagents bearing C3F7, C4F9, and C6F13 chains were prepared on multi-gram scale (ca. 1.0-7.0 g) in eight steps with overall yields of 73%, 60%, and 90%, respectively. The order of addition of the fluorous alkenes in a one-pot double tagging Heck reaction was also investigated in order to conduct an encoded mixture synthesis of f-Fmoc reagents. The target f-Fmoc reagents bearing C3F7, C4F9, and C6F13 chains could be effectively separated based on the fluorine content of the molecules. (C) 2015 Elsevier Ltd. All rights reserved.