9H-fluoren-9-ylmethyl N-[(2S)-1-azido-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propan-2-yl]carbamate | 391624-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-[(2S)-1-azido-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propan-2-yl]carbamate
• CAS: 391624-31-0
• 化学式: C₂₈H₃₀N₄O₃
• 分子量: 470.571
• InChiKey: BCSDLDNRWDECBV-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-[(2S)-1-azido-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propan-2-yl]carbamate 在 10percent Pd/C 氢气 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 [(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propyl]azanium;chloride
  参考文献：
  名称：

  Solid-Phase Synthesis of Oligourea Peptidomimetics Employing the Fmoc Protection Strategy

  摘要：

  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).

  DOI：

  10.1021/jo010656q
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl [(1S)-1-(4-tert-butoxybenzyl)-2-hydroxyethyl]carbamate 在 咪唑 、 sodium azide 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 9H-fluoren-9-ylmethyl N-[(2S)-1-azido-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propan-2-yl]carbamate
  参考文献：
  名称：

  Mild and Efficient Synthesis of Fmoc-Protected Amino Azides from Fmoc-Protected Amino Alcohols

  摘要：

  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。

  DOI：

  10.1055/s-2005-923589

文献信息

• Staudinger/aza-Wittig reaction to access<i>N</i>^β-protected amino alkyl isothiocyanates
  作者：L. Santhosh、S. Durgamma、Shekharappa Shekharappa、Vommina V. Sureshbabu

  DOI：10.1039/c8ob01061g

  日期：——

  A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols;

  一种统一的方式来访问Ñ β -保护的氨基烷基异硫氰酸酯使用Ñ β描述了通过Staudinger / aza-Wittig反应的一般策略保护的氨基烷基叠氮化物。用于获得异硫氰酸酯的方案的类型取决于前体的可用性，尤其是在氨基酸化学中，还取决于其他不稳定基团对方案中所用试剂的行为。幸运的是，我们并不担心这两个因素，因为通过标准方案可以轻松制备前体叠氮化物，并且本方案可以为访问标题化合物铺平道路，而不会影响Boc，Cbz和Fmoc保护基以及苄基和叔丁基。侧链。本策略消除了使用胺来获得标题化合物的需要，因此，该方法是分步经济的。其他优点包括保留手性，方便处理和易于纯化。还制备了一些迄今未报告的化合物，所有最终化合物均通过IR，质量，旋光度和1 H和13 C NMR研究。
• 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.