(9H-fluoren-9-yl)methyl ((2S,3S)-1-iodo-3-methylpentan-2-yl)carbamate | 1172596-35-8

• 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 ((2S,3S)-1-iodo-3-methylpentan-2-yl)carbamate
• CAS: 1172596-35-8
• 化学式: C₂₁H₂₄INO₂
• 分子量: 449.332
• InChiKey: YRSOEUWXXYGJFT-VBKZILBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl ((2S,3S)-1-iodo-3-methylpentan-2-yl)carbamate 在 10% palladium on carbon 、 氢气 作用下， 生成 9H-fluoren-9-ylmethyl N-[(2S,3S)-1-amino-3-methylpentan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis of Thioureido-Linked Peptidomimetics, Glycosylated Amino Acids, and Neoglycoconjugates Using Bis(benzotriazolyl)methanethione as Thioacylating Agent

  摘要：

  本文描述了一种实用的硫脲连接肽模拟物、糖基化氨基酸和新生糖缀合物的综合合成方法，采用双（苯并三唑基）甲烷硫酮作为硫羰基化试剂。整个方案温和、高效、产率高，并且不含危险试剂。所有中间体和产物均已分离并通过¹H NMR、¹³C NMR 和质谱完全表征。

  DOI：

  10.1055/s-0029-1219393
• 作为产物：
  描述：

  Fmoc-异leucinol 在 咪唑 、 碘 、 三苯基膦 作用下， 生成 (9H-fluoren-9-yl)methyl ((2S,3S)-1-iodo-3-methylpentan-2-yl)carbamate
  参考文献：
  名称：

  一种合成新型二硫代氨基甲酸酯连接的拟肽的简单方法

  摘要：

  描述了合成一系列新的二硫代氨基甲酸酯连接的拟肽的有效方案。由氨基酸酯与二硫化碳在三乙胺存在下反应形成的原位生成的二硫代氨基甲酸中间体用N保护的氨基烷基碘处理，以良好至中等的收率得到标题化合物3a – g。还描述了含有两个二硫代氨基甲酸酯键的N -Fmoc保护的三肽模拟物4a – e的合成。该协议被进一步扩展为合成N，N'-正交保护的二硫代氨基甲酸酯连接的二肽模拟物7a – c也一样 温和的反应条件和无毒试剂是本方法的优点。

  DOI：

  10.1016/j.tetlet.2009.09.172

文献信息

• Synthesis of chiral N^β-protected amino diselenides from the corresponding amino alkyl iodides using NaBH₂Se₃ as a selenating reagent and their conversion to seleninic acids
  作者：Nageswara Rao Panguluri、Veladi Panduranga、Girish Prabhu、T. M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1039/c5ra06147d

  日期：——

  been presented for the synthesis of Nβ-protected amino diselenides from the corresponding amino alkyl iodides using in situ generated NaBH2Se3 as an efficient selenating reagent. All the diselenides are obtained in good yields under very mild conditions, short duration times and the protocol is free from racemization. The methodology has been effectively extended to the synthesis of N-protected L-selenocystine

  一种方便的方法已被提出对于N的合成β -保护氨基diselenides从使用相应的氨基烷基碘在原位生成的NaBH 2硒3作为一种有效的试剂selenating。所有二硒化物都在非常温和的条件下，短的持续时间下以高收率获得，并且该方案没有消旋作用。该方法已经有效地扩展到了N-保护的L-硒代胱氨酸甲酯的合成。N个干净氧化β -保护的氨基diselenides到N β -保护的氨基酸亚硒酸使用35％含水ħ 2 ö 2也已经完成。本方案与所有常见的氨基甲酸酯保护基相容。
• Synthesis of an amino phosphinodiselenoic acid ester and β-amino diselenides employing P₂Se₅
  作者：L. Roopesh Kumar、N. R. Sagar、K. Divya、C. Madhu、Vommina V Sureshbabu

  DOI：10.1039/d0nj00012d

  日期：——

  The synthesis of a new class of amino phosphinodiselenoic acid ester and β-amino diselenides is conducted by employing a reaction between Nβ-protected aminoalkyl iodide and phosphorus pentaselenide (P2Se5) has been described. In the presence of protic solvents, amino phosphinodiselenoic acid esters were found to be the major products, whereas β-amino diselenides were formed exclusively when the reaction

  一类新的氨基phosphinodiselenoic酸酯和β氨基diselenides的合成通过采用之间的反应进行Ñ β -保护的氨基烷基碘和磷pentaselenide（P 2硒5）进行了说明。在质子溶剂存在下，发现氨基膦基二硒酸酯是主要产物，而β-氨基二硒化物仅在极性非质子溶剂中进行反应时形成。
• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
• Peptidotriazoles with antimicrobial activity against bacterial and fungal plant pathogens
  作者：Imma Güell、Lluís Micaló、Laura Cano、Esther Badosa、Rafael Ferre、Emilio Montesinos、Eduard Bardají、Lidia Feliu、Marta Planas

  DOI：10.1016/j.peptides.2011.12.003

  日期：2012.1

  We designed and prepared peptidotriazoles based on the antimicrobial peptide BP100 (LysLysLeuPheLysLysIleLeuLysTyrLeu-NH2) by introducing a triazole ring in the peptide backbone or onto the side chain of a selected residue. These compounds were screened for their in vitro growth inhibition of bacterial and fungal phytopathogens, and for their cytotoxic effects on eukaryotic cells and tobacco leaves. Their proteolytic susceptibility was also analyzed. The antibacterial activity and the hemolysis were influenced by the amino acid that was modified with the triazole as well as by the absence of presence of a substituent in this heterocyclic ring. We identified sequences active against the bacteria Xanthomonas axonopodis pv. vesicatoria, Erwinia amylovora, Pseudomonas syringae pv. syringae (MIC of 1.6-12.5 mu M), and against the fungi Fusarium oxysporum (MIC < 6.2-12.5 mu M) with low hemolytic activity (0-23% at 50 mu M), high stability to protease digestion and no phytotoxicity. These peptidotriazoles constitute good candidates to design new antimicrobial agents. (C) 2011 Elsevier Inc. All rights reserved.