2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(tertbutyldimethylsilyloxy)phenyl)propanoic acid | 146346-83-0

• 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: 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(tertbutyldimethylsilyloxy)phenyl)propanoic acid
• 英文别名: Fmoc-Tyr(Tbdms)-OH；Fmoc-Tyr-OTBDMS；Fmoc-Tyr(TBDMS)(TBDMS)-OH；(2S)-3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 146346-83-0
• 化学式: C₃₀H₃₅NO₅Si
• 分子量: 517.697
• InChiKey: CQIORESQZRVISK-MHZLTWQESA-N

物化性质

• 熔点：
  92-93 °C
• 沸点：
  642.6±55.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(tertbutyldimethylsilyloxy)phenyl)propanoic acid 在 叔丁基过氧化氢 、 溶剂黄146 作用下， 生成 (S)-2-((((9H-芴-9-基)甲氧基)羰基)氨基)-3-(4-((双(苄氧基)磷酰基)氧基)苯基)丙酸
  参考文献：
  名称：

  制备和使用的Ñ α -fluorenylmethoxycarbonyl- ö -dibenzylphosphono -L-酪氨酸在连续流动固相肽合成

  摘要：

  Ñ α -Fluorenylmethoxycarbonyl- ö -dibenzylphosphono-大号-酪氨酸是用于固相合成中的有用的衍生物ö -phosphotyrosine肽。

  DOI：

  10.1039/c39910000338
• 作为产物：
  描述：

  Fmoc-Tyr-O-All 在 咪唑 、 四(三苯基膦)钯 、 N-甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(tertbutyldimethylsilyloxy)phenyl)propanoic acid
  参考文献：
  名称：

  磺肽的发散和位点选择性固相合成

  摘要：

  扎实的基础：描述了有效合成磺肽的固相策略。正交保护的酪氨酸残基的选择性脱保护和固相硫酸化提供了高收率差异化获得差异化硫酸化肽的途径。

  DOI：

  10.1002/asia.201100232

文献信息

• Total Synthesis of Scytonemide A Employing Weinreb AM Solid-Phase Resin
  作者：Tyler A. Wilson、Robert J. Tokarski、Peter Sullivan、Robert M. Demoret、Jimmy Orjala、L. Harinantenaina Rakotondraibe、James R. Fuchs

  DOI：10.1021/acs.jnatprod.7b00912

  日期：2018.3.23

  biomimetic solid-phase peptide synthesis (SPPS) approach employing the Weinreb AM resin. Utilizing this approach, cyclization of the protected heptapeptide via formation of the imine bond occurred spontaneously upon cleavage from the resin in the presence of a reducing agent and subsequent aqueous workup. The final deprotection step necessary to produce the natural product was accomplished under slightly

  人 20S 蛋白酶体抑制剂 scytonemide A ( 1 ) 是一种大环亚胺，最初从蓝藻Scytonema hofmanni中分离出来，采用 Weinreb AM 树脂通过仿生固相肽合成 (SPPS) 方法合成。利用这种方法，受保护的七肽在还原剂存在下从树脂上裂解并随后进行水处理后，通过形成亚胺键自发地发生环化。生产天然产物所需的最终脱保护步骤是在弱碱性条件下完成的，促进甲硅烷基醚基团的裂解，同时保持大环完整。合成的 scytonemide A 的纯化是通过正相快速柱色谱完成的，有可能促进未来机理和 SAR 研究所需的化合物的大规模制备。目标化合物的结构通过 NMR 光谱得到证实，这也揭示了合成和天然 scytonAMide A 样品获得的光谱数据的差异，其中1 H NMR 光谱中的一些酰胺和醇信号。
• Templated Total Synthesis of Cu(I)‐Methanobactin OB3b**
  作者：Emilia Cupioli、Frédéric J. M. Gaigne、Anna Sachse、Philipp Buday、Wolfgang Weigand、Phil Liebing、Hans‐Dieter Arndt

  DOI：10.1002/anie.202304901

  日期：2023.10.16

  The first total synthesis of Cu(I)-methanobactin OB3b, a unique carcerand-like chalkophore, is reported. Key features were a cyclodehydratation-thioacylation sequence for accessing two unprecedented azlactone building blocks and metal ion-templation for enabling cyclization of the methanobactin peptide backbone.

  首次全合成了 Cu(I)-methanobactin OB3b（一种独特的类癌菌素）。主要特征是用于获得两种前所未有的吖内酯结构单元的环脱水-硫代酰化序列和用于实现甲烷杆菌肽主链环化的金属离子模板。
• “One pot” synthesis of quinazolinone-[2,3]-fused polycyclic scaffolds in a three-step reaction sequence
  作者：Yuanmu Zhang、Lingxuan Zhu、Yi Lu、Xinsheng Lei、Yingxia Li

  DOI：10.1039/d4ob00529e

  日期：——

  skeletons occupy a prominent position in drug discovery. Even with currently available methods there still remain unmet needs for flexible access to such structures. Herein, we have explored a mild “one pot” procedure for the construction of various quinazolinone-[2,3]-fused polycycles. The procedure involves Pd-catalyzed carbonylation of N-(2-iodophenyl)acetamides, release of the masked terminal amine

  多种喹唑啉酮-[2,3]-稠合多环骨架在药物发现中占据着重要地位。即使采用当前可用的方法，对于灵活访问此类结构的需求仍然未得到满足。在此，我们探索了一种温和的“一锅法”程序来构建各种喹唑啉酮-[2,3]-稠合多环。该过程包括 Pd 催化的N- (2-碘苯基)乙酰胺的羰基化、掩蔽末端胺的释放以及两个连续的自发环化。这种普遍适用的方法具有从容易获得的起始材料中轻松组装前体、反应条件温和、操作不繁琐和多环多样性的特点。
• Azapeptide Analogues of the Growth Hormone Releasing Peptide 6 as Cluster of Differentiation 36 Receptor Ligands with Reduced Affinity for the Growth Hormone Secretagogue Receptor 1a
  作者：Caroline Proulx、Émilie Picard、Damien Boeglin、Petra Pohankova、Sylvain Chemtob、Huy Ong、William D. Lubell

  DOI：10.1021/jm300557t

  日期：2012.7.26

  The synthetic hexapeptide growth hormone releasing peptide-6 (GHRP-6) exhibits dual affinity for the growth hormone secretagogue receptor la (GHS-R1a) and the cluster of differentiation 36 (CD36) receptor. Azapeptide GHRP-6 analogues have been synthesized, exhibiting micromolar affinity to the CD36 receptor with reduced affinity toward the GHS-R1a. A combinatorial split-and-mix approach furnished aza-GHRP-6 leads, which were further examined by alanine scanning. Incorporation of an aza-amino acid residue respectively at the D-Trp(2) Ala(3), or Trp(4) position gave aza-GHRP-6 analogues with reduced affinity toward the GHS-R1a by at least a factor of 100 and in certain cases retained affinity for the CD36 receptor. In the latter cases, the D-Trp2 residue proved important for CD36 receptor affinity; however, His' could be replaced by Ala' without considerable loss of binding. In a microvascular sprouting assay using a choroid explant, [azaTyr(4)]-GHRP-6 (15), [Ala(1), azaPhe(2)]-GHRP-6 (16), and [azaLeu(3), Ala(6)]-GHRP-6 (33) all exhibited antiangiogenic activity.
• Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis
  作者：Peter M. Fischer

  DOI：10.1016/s0040-4039(00)60836-5

  日期：——

  The utility of Tbdms (t-butyldimethylsilyl) ethers, prepared conveniently in a one-pot procedure from N(alpha)-Fmoc (9-fluorenylmethoxycarbonyl) and N(alpha)-Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives. The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains after peptide chain assembly, desirable, e.g., for phosphorylation or glycosilation.