9H-fluoren-9-ylmethyl N-[(2S)-1-hydroxy-3-methylpentan-2-yl]carbamate | 410082-62-1

• 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-hydroxy-3-methylpentan-2-yl]carbamate
• CAS: 410082-62-1
• 化学式: C₂₁H₂₅NO₃
• 分子量: 339.434
• InChiKey: YMPMFRNXDNCNRH-YBMSBYLISA-N

物化性质

• 沸点：
  525.2±33.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-[(2S)-1-hydroxy-3-methylpentan-2-yl]carbamate 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 以80%的产率得到((S)-1-Azidomethyl-2-methyl-butyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  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：

  N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isoleucine 在 N-甲基吗啉 、 sodium tetrahydroborate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 1.0h， 以95%的产率得到9H-fluoren-9-ylmethyl N-[(2S)-1-hydroxy-3-methylpentan-2-yl]carbamate
  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

文献信息

• Efficient Synthesis of <i>N</i>-Fmoc-Aminoalkoxy Pentafluorophenyl Carbonates: Application for the Synthesis of Oligopeptidyl Carbamates
  作者：Vommina V. Sureshbabu、H. P. Hemantha

  DOI：10.1080/00397910902790378

  日期：2009.9.8

  N-Fmoc--Aminoalkoxy pentafluorophenyl carbonates have been synthesized through the reaction of N-Fmoc--aminoalkoxy carbonyl chloride with pentafluorophenol. The reaction was clean and high yielding, and the products have been fully characterized using infrared, NMR, and mass spectroscopy. Their utility as efficient building blocks for the preparation of N-Fmoc-oligopeptidyl carbamate esters and acids has been demonstrated. The method exemplifies a simple protocol for the efficient preparation of oligopeptidyl carbamates in solution phase.
• Efficient loading of primary alcohols onto a solid phase using a trityl bromide linker
  作者：François Crestey、Lars K. Ottesen、Jerzy W. Jaroszewski、Henrik Franzyk

  DOI：10.1016/j.tetlet.2008.07.130

  日期：2008.10

  The Letter describes an improved, rapid and mild strategy for the loading of primary alcohols onto a polystyrene trityl resin via a highly reactive trityl bromide linker. This protocol facilitates an efficient resin loading even of acid-sensitive or heat-labile alcohols, which otherwise require expensive or non-commercial resin types. Secondary alcohols were only attached in moderate to low yields, while attempts to load a tertiary alcohol expectedly failed. Importantly, selective attachment of diols via a primary alcohol group in the presence of more hindered alcohol groups proved possible. The effects of activation time and reagent excess as well as alcohol structure were investigated. This improved method provides a convenient access to O-linked resin-bound N-Fmoc-protected amino alcohols that may be employed in SPS of peptides with C-terminal alcohol functionalities. In the case of a sensitive alcohol containing an activated aziridine functionality, the use of the trityl bromide linker proved superior to a recently described silver triflate-assisted trityl chloride resin-based Procedure. (C) 2008 Elsevier Ltd. All rights reserved.
• Oxidizing Polymers: A Polymer-Supported, Recyclable Hypervalent Iodine(V) Reagent for the Efficient Conversion of Alcohols, Carbonyl Compounds, and Unsaturated Carbamates in Solution J.R. gratefully acknowledges generous support from Prof. M. E. Maier, Tübingen, the Strukturfonds of the University of Tübingen, the Fonds der Chemischen Industrie, and the DFG. We thank Graeme Nicholson, Dietmar Schmid, and Daniel Bischoff for analytical support.
  作者：Gerhard Sorg、Anne Mengel、Günther Jung、Jörg Rademann

  DOI：10.1002/1521-3773(20011203)40:23<4395::aid-anie4395>3.0.co;2-r

  日期：2001.12.3