(9H-fluoren-9-yl)methyl tert-butyl(6-azidohexane-1,5-diyl)-(S)-dicarbamate | 391624-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl tert-butyl(6-azidohexane-1,5-diyl)-(S)-dicarbamate
• 英文别名: Fmoc-Lys(Boc)-N3；tert-butyl N-[(5S)-6-azido-5-(9H-fluoren-9-ylmethoxycarbonylamino)hexyl]carbamate
• CAS: 391624-34-3
• 化学式: C₂₆H₃₃N₅O₄
• 分子量: 479.579
• InChiKey: QPTFTYANGKYMKH-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl tert-butyl(6-azidohexane-1,5-diyl)-(S)-dicarbamate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以100%的产率得到((S)-5-Amino-6-azido-hexyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  在β位置带有赖氨酸侧链的肽核酸：DNA切割的合成和应用。

  摘要：

  本文报道了新的β-Lys肽核酸（PNA）单体的合成及其掺入10个残基的PNA序列。含有β-LysPNA单元的PNA与DNA形成了稳定的杂交双链体。但是，β-LysPNA单元的并入会在一定程度上引起PNA-DNA双链体的不稳定。β-PNA和DNA之间的静电吸引力可能会降低这种去稳定作用。随后，制备联吡啶结合的β-LysPNA，并表现出DNA的序列选择性切割。基于裂解产物的结构和分子建模，我们推断联吡啶部分位于PNA-DNA双链体的小沟内。β-PNA的赖氨酸侧链是用于连接各种功能分子的多功能手柄。

  DOI：

  10.1248/cpb.c16-00191
• 作为产物：
  描述：

  [(S)-5-(9H-Fluoren-9-ylmethoxycarbonylamino)-6-iodo-hexyl]-carbamic acid tert-butyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到(9H-fluoren-9-yl)methyl tert-butyl(6-azidohexane-1,5-diyl)-(S)-dicarbamate
  参考文献：
  名称：

  在β位置带有赖氨酸侧链的肽核酸：DNA切割的合成和应用。

  摘要：

  本文报道了新的β-Lys肽核酸（PNA）单体的合成及其掺入10个残基的PNA序列。含有β-LysPNA单元的PNA与DNA形成了稳定的杂交双链体。但是，β-LysPNA单元的并入会在一定程度上引起PNA-DNA双链体的不稳定。β-PNA和DNA之间的静电吸引力可能会降低这种去稳定作用。随后，制备联吡啶结合的β-LysPNA，并表现出DNA的序列选择性切割。基于裂解产物的结构和分子建模，我们推断联吡啶部分位于PNA-DNA双链体的小沟内。β-PNA的赖氨酸侧链是用于连接各种功能分子的多功能手柄。

  DOI：

  10.1248/cpb.c16-00191

文献信息

• Mild and Efficient Synthesis of Fmoc-Protected Amino Azides from Fmoc-Protected Amino Alcohols
  作者：Erkang Fan、Somnath Mondal

  DOI：10.1055/s-2005-923589

  日期：——

  Fmoc-protected amino azides - key intermediates for monomers of oligomeric urea and guanidine - can be efficiently prepared from the corresponding amino alcohol through iodination followed by substitution with sodium azide. This synthetic route avoids the preparation, storage, and handling of the highly toxic azidic acid that is used in an alternative method.

  Fmoc保护的氨基叠氮化物 - 聚氨基脲和胍的单体关键中间体 - 可以通过碘化和随后用叠氮化钠取代的方法，从相应的氨基醇高效制备。该合成路线避免了在另一种方法中制备、储存和处理高度毒性的叠氮酸。
• Solid-Phase Synthesis of Oligourea Peptidomimetics Employing the Fmoc Protection Strategy
  作者：Astrid Boeijen、Jeroen van Ameijde、Rob M. J. Liskamp

  DOI：10.1021/jo010656q

  日期：2001.12.1

  A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).
• Solid-Phase Synthesis of Azidomethylene Inhibitors Targeting Cysteine Proteases
  作者：Peng-Yu Yang、Hao Wu、Mei Yin Lee、Ashley Xu、Rajavel Srinivasan、Shao Q. Yao

  DOI：10.1021/ol800575z

  日期：2008.5.1

  An efficient strategy for the solid-phase synthesis of azidomethylene inhibitors targeting cysteine proteases is described. The method is highlighted by its compatibility with readily available building blocks, as well as its ability to accommodate different functional groups. A 249-member library has thus far been successfully synthesized, characterized, and screened against Caspase-1, -3 and -7.
• Solid-Phase and Solution-Phase Syntheses of Oligomeric Guanidines Bearing Peptide Side Chains
  作者：Zhongsheng Zhang、Erkang Fan

  DOI：10.1021/jo051226t

  日期：2005.10.1

  Synthetic strategies for preparing N,N'-bridged oligomeric guanidines bearing peptide side chains both on solid support and in solution are presented. Monomers are prepared from common a-amino acids and therefore contain conventionally protected peptide side chains. The side chains include alkyl, aromatic, hydroxyl, amino, carboxylic acid, and amide functional groups. Oligomer elongation utilizes acid-sensitive sulfonyl activated thiourea through the formation of carbodiimide intermediate. With proper preparation of monomers, synthesis of oligomer can be performed in two directions (equivalent to N to C terminal or C to N terminal in a peptide sequence) with excellent efficiency.
• Solid phase synthesis of peptidotriazoles with multiple cycles of triazole formation
  作者：Zhongsheng Zhang、Erkang Fan

  DOI：10.1016/j.tetlet.2005.11.111

  日期：2006.1

  Peptidotriazoles, unnatural oligomers with alternating amide and triazole linkages, are synthesized efficiently on solid support. The key transformations involve multiple cycles of 1,2,3-triazolc formation, using soluble Cu(I) catalyst and conditions that do not generate precipitate on solid support nor require exclusion of oxygen. Our synthetic protocol will enable the preparation of other unnatural oligomers with multiple triazoles using solid phase methodologies. (c) 2005 Elsevier Ltd. All rights reserved.