4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-pentanoic acid tert-butyl ester | 290292-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-pentanoic acid tert-butyl ester
• 英文别名: (9H-fluoren-9-yl)methyl (S)-4-(tert-butoxycarbonyl)-1-iodobutan-2-ylcarbamate；tert-butyl 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-iodopentanoate；tert-butyl (4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodopentanoate
• CAS: 290292-97-6
• 化学式: C₂₄H₂₈INO₄
• 分子量: 521.395
• InChiKey: JJIDEMOWPQVRSL-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-pentanoic acid tert-butyl ester 在 三乙基硅烷 、 sodium azide 、 sodium ascorbate 、 二乙胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 0.5h， 生成 (S)-5-(4-((R)-1-amino-2-hydroxyethyl)-1H-1,2,3-triazol-1-yl)-4-(3-((1S,2S)-1-carboxy-2-hydroxypropyl)ureido)pentanoic acid
  参考文献：
  名称：

  作为PD-L1抑制剂的杂环类化合物

  摘要：

  本发明属于医药化学领域，涉及一类作为PD‑L1抑制剂的杂环类化合物及其应用，具体地，本发明涉及式A所示的化合物或其异构体、药学上可接受的盐、溶剂化物或前药，它们的制备方法以及含有这些化合物的药物组合物和这些化合物或组合物用于治疗癌症或者感染类疾病的用途。

  公开号：

  CN108863963B
• 作为产物：
  描述：

  Fmoc-O-叔丁基-L-谷氨酸 在 四碘化二磷 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二硫化碳 、 乙酸乙酯 为溶剂， 反应 0.67h， 生成 4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  P2I4试剂超声加速氨基醇合成N-保护氨基烷基碘及其在氨基烷基硫醇合成中的应用

  摘要：

  氨基酸衍生的烷基碘的合成产生了许多肽模拟物的通用中间体，因此，在本工作中实现了在中性条件下合成它们的方法。在 T3P 作为活化剂和 NaBH4 作为还原剂的作用下，N-保护的氨基酸被还原为氨基醇。因此，合成的氨基醇在CS2中用四碘化二磷(P2I4)超声处理以获得N-保护的氨基烷基碘。我们通过将烷基碘转化为氨基烷基硫醇来确定其用途，氨基烷基硫醇可作为许多杂环和其他候选药物的构建单元。超声介质对所有中间体的制备均有效；条件温和，所有步骤的收率几乎都是定量的。合成的化合物通过1H NMR、13C NMR和HRMS分析进行表征。

  DOI：

  10.2174/1570178620666230913160751

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。
• <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).
• Structure−Affinity Relationships of Glutamine Mimics Incorporated into Phosphopeptides Targeted to the SH2 Domain of Signal Transducer and Activator of Transcription 3
  作者：Pijus K. Mandal、Zhiyong Ren、Xiaomin Chen、Chiyi Xiong、John S. McMurray

  DOI：10.1021/jm901105k

  日期：2009.10.8

  In cancer cells, signal transducer and activator of transcription 3 (Stat3) participates in aberrant growth, survival, angiogenesis, and invasion signals and is a validated target for anticancer drug design. We are targeting its SH2 domain to prevent docking to cytokine and growth factor receptors and subsequent signaling. One of the important elements of the recognition sequence, pTyr-Xxx-Xxx-Gln, is glutamine. We incorporated novel Gin mimics into a lead peptide, pCinn-Leu-Pro-Gln-NHBn, and found that a linear, unconstrained side chain and carboxamide are necessary for high affinity, and the benzamide can be eliminated. Replacement of Gln-NHBn with (R)-4-aminopentanamide or 2-aminoethylurea produced inhibitors with equal or greater potency than that of the lead, as judged by fluorescence polarization (IC50 values were 110 and 130 nM, respectively). When Pro was replaced with cis-3,4-methanoproline, the glutamine mimic, (4R,5S)-4-amino-5-benzyloxyhexanamide resulted in an IC50 of 69 nM, the highest affinity Stat3 inhibitor reported to date.
• Straightforward Entry to <i>S</i>-Glycosylated Fmoc-Amino Acids and Their Application to Solid Phase Synthesis of Glycopeptides and Glycopeptidomimetics
  作者：Daniela Comegna、Ivan de Paola、Michele Saviano、Annarita Del Gatto、Laura Zaccaro

  DOI：10.1021/ol503664t

  日期：2015.2.6

  Streamlined access to S-glycosylated Fmoc-amino acids was developed. The process provides diverse glycosylated modified amino acids in high yield and stereoselectivity taking advantage of the in situ generation of a glycosylthiolate obtained from carbohydrate acetates in a few steps. Mild basic conditions make the conjugation reaction compatible with Fmoc-iodo-amino acids. To validate the strategy the glycosylated building blocks were used for SPPS and the unprecedented incorporation of a long thio-oligosaccharide to the peptide chain was demonstrated.
• Solid-Phase Synthesis of New <i>S</i>-Glycoamino Acid Building Blocks
  作者：Laurence Jobron、Gerd Hummel

  DOI：10.1021/ol006019o

  日期：2000.7.1

  [GRAPHICS]Efficient synthesis of unprotected S-glycoamino acid building blocks in the solid phase by coupling a sugar 1-thiolate with iodine activated fluoren-9-ylmethoxycarbonyl (Fmoc) protected amino acids.