(9H-fluoren-9-yl)methyl 1-azido-4-methyl-1-oxopentan-2-ylcarbamate | 329308-97-6

• 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: (9H-fluoren-9-yl)methyl 1-azido-4-methyl-1-oxopentan-2-ylcarbamate
• 英文别名: Fmoc-Leu-N3；9H-fluoren-9-ylmethyl N-[(2S)-1-azido-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 329308-97-6
• 化学式: C₂₁H₂₂N₄O₃
• 分子量: 378.431
• InChiKey: UQJHLVITMKQOEX-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl 1-azido-4-methyl-1-oxopentan-2-ylcarbamate 生成 p-nitrophenyl {1-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}-3-methylbutyl}carbamate
  参考文献：
  名称：

  Patil, Basanagoud S.; Suresh Babu, Vommina V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 8, p. 1721 - 1728

  摘要：

  DOI：
• 作为产物：
  描述：

  Fmoc-L-亮氨酸 在 N-甲基吗啉 、 sodium azide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.83h， 生成 (9H-fluoren-9-yl)methyl 1-azido-4-methyl-1-oxopentan-2-ylcarbamate
  参考文献：
  名称：

  电喷雾电离串联质谱（ESI-MS / MS）对Nα-Fmoc保护的脲肽的表征：位置异构体的区分

  摘要：

  四对脲肽位置异构体，FmocNH-CH（R 1）-φ（NH-CO-NH）-CH（R 2）-OY和FmocNH-CH（R 2）-φ（NH-CO-NH）- CH（R 1）-OY（Fmoc = [（9-芴基甲基）氧基]羰基; R 1 = H，烷基; R 2 =烷基，H和Y = CH 3 / H），已通过两种方法进行了表征和区分正离子和负离子电喷雾电离（ESI）离子阱串联质谱（MS / MS）。在MS注意到主要分段/所有这些化合物的MS是由于 Ñ  CH（R） Ñ 键裂解形成特征性的N和C端碎片离子。N端的甘氨酸衍生的质子化的尿苷肽酸在m / z 240时形成质子化的（9H-芴-9-9）甲基氨基甲酸酯离子，而相应的酯则不存在。在N端衍生自甘氨酸的尿苷肽中发现的另一个有趣的片段化是中间片段离子FmocNH = CH 2 +（m / z 252）导致的61个单位的异常丢失。一种涉及离子中性络合物以及NH

  DOI：

  10.1002/jms.1862

文献信息

• New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: application of peptide coupling agents EDC and HBTU
  作者：Vommina V. Sureshbabu、H. S. Lalithamba、N. Narendra、H. P. Hemantha

  DOI：10.1039/b920290k

  日期：——

  Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved.

  使用肽偶联剂，EDC和 HBTU描述。该程序高效，实用并且适用于多种羧酸，包括ñ保护的氨基酸。使用相同的试剂，还可以从酸一锅合成尿素，二肽基脲酯和氨基甲酸酯。
• An Efficient Conversion of the Carboxylic Group of <i>N</i>-Fmoc α-Amino Acids/Peptide Acids into <i>N</i>-Formamides Employing Isocyanates as Key Intermediates
  作者：N. S. Sudarshan、N. Narendra、H. P. Hemantha、Vommina V. Sureshbabu

  DOI：10.1021/jo701371k

  日期：2007.12.1

  [Graphics]Reaction of 96% formic acid with isocyanates derived from N-Fmoc alpha-amino acids/peptide acids catalyzed by DMAP has yielded a new class of stable formamides as crystalline solids which have been characterized by IR, H-1 NMR, C-13 NMR, and mass spectroscopy. Conversion of the side chain carboxylic acid of N-Fmoc-5-oxazolidinones of Asp/Glu into the N-formyl group also has been accomplished. The reaction is simple, mild, and high yielding.
• Synthesis of <i>N</i> ^{<font>α</font>}-Protected Amino Acid–Derived Selenocarbamates Employing Isocyanates as Key Intermediates
  作者：Vommina V. Sureshbabu、Shankar A. Naik

  DOI：10.1080/00397910903318641

  日期：2010.8.16

  A simple protocol for the synthesis of N-urethane-protected N-alkyl-Se-alkyl selenocarbamate derivatives of amino acids has been described. The reaction of N-urethane-protected amino alkyl isocyanates with selenating agent LiAlHSeH and subsequent coupling with an alkyl halide yielded the title compounds in good yield and purity. All the selenocarbamates obtained have been characterized by 1H NMR, 13C NMR, and mass spectral studies.
• Babu, Vommina V. Suresh; Ananda, Kuppanna; Vasanthakumar, Ganga-Ramu, Journal of the Chemical Society. Perkin transactions I, 2000, # 24, p. 4328 - 4331
  作者：Babu, Vommina V. Suresh、Ananda, Kuppanna、Vasanthakumar, Ganga-Ramu

  DOI：——

  日期：——
• Synthesis of retro-inverso peptides employing isocyanates of Nα-Fmoc-amino acids/peptide acids catalyzed by DMAP
  作者：Rao Venkataramanarao、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2006.10.066

  日期：2006.12

  The Goldschmidt-Wick type reaction between isocyanates of N-alpha-Fmoc-amino acids/peptide acids and N-alpha-Boc-/Z-/ Bsmoc-amino acids catalyzed by DMAP leads to the incorporation of a reversed peptide bond. It was found to be a simple, efficient and clean reaction. All the retro-inverso peptides made were obtained as crystalline compounds in 70-92% yields. (c) 2006 Elsevier Ltd. All rights reserved.