Fmoc-Ser-NHBn | 929294-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Ser-NHBn
• 英文别名: (S)-(9H-fluoren-9-yl)methyl(1-(benzylamino)-3-hydroxy-1-oxopropan-2-yl)carbamate
• CAS: 929294-60-0
• 化学式: C₂₅H₂₄N₂O₄
• 分子量: 416.477
• InChiKey: ZSBWGVJCNRGFKT-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Ser-NHBn 、 3-(triethylsilyl)propyl isocyanate 在 dibutyltin(II) dilaurate 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  l-serine-functionalized montmorillonite decorated with Au nanoparticles: A new highly efficient catalyst for the reduction of 4-nitrophenol

  摘要：

  The conversion of nitroarenes to aminoarenes is of great industrial interest since they are prevalent pollutants in water and aminoarenes are important intermediates in the synthesis of pharmaceuticals, natural products and in bulk chemical production. In this work, two new catalysts for the reduction of 4-nitrophenol (4-NP) to 4-aminophenol (4-AP) were prepared by immobilization of gold nanoparticles onto the surface of K10 montmorillonite clay (K10) functionalized with two new L-serine derivative organosilanes. Transmission electron microscopy showed the presence of 4-5 nm gold nanoparticles after catalysis. The reduction reaction of 4-NP to 4-AP at 25 degrees C, using NaBH4 as reducing agent, led to nearly 100% conversion in only 1 minute, presenting pseudo-first-order rate constants normalized for Au loading of K = 630 and 430 mmol(-1) s(-1). The catalysts showed high stability, leading to substrate conversions of 95-100% after 10 consecutive cycles, with negligible Au leaching. (C) 2018 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2018.02.027
• 作为产物：
  描述：

  FmocSer(tBu)NHBn 在 三氟乙酸 作用下， 生成 Fmoc-Ser-NHBn
  参考文献：
  名称：

  Solid-phase synthesis of Stat3 inhibitors incorporating O-carbamoylserine and O-carbamoylthreonine as glutamine mimics

  摘要：

  O-Carbamoyiserine and O-carbamoylthreonine are glutamine analogues that were incorporated into a Stat3 inhibitory peptide to probe the requirements of Gin at the pY+3 position. Fmoc-Ser-NHBn and Fmoc-Thr-NHBn were converted to nitrophenyl carbonates and were attached to Rink resin via a side-chain carbamate linkage. After assembly of the peptide, acid treatment resulted in O-carbamoylserine and O-carbamoylthreonine-containing peptides. The order of affinity for Stat3 was Gin > Ser (CONH2) > Thr(CONH2) suggesting a relatively tight binding pocket for the side chain of glutamine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.099

文献信息

• Exploration of the Fluoride Reactivity of Aryltrifluoroborate on Selective Cleavage of Diphenylmethylsilyl Groups
  作者：Katsumasa Fujiki、Katsunori Tanaka

  DOI：10.1002/ejoc.202000707

  日期：2020.8.9

  substituents on the benzene ring. The fluorine on trifluoroborate interacts with silicon and activates the Si–O bond to enable selective desilylation of the diphenylmethylsilyl group. Selective desilylation of a primary silyl ether in the presence of a secondary silyl ether by the trifluoroborate was also successful.

  三氟硼酸苯酯在二苯基甲基甲硅烷基的去甲硅烷基化中独特的氟化物反应性受苯环上的取代基控制。三氟硼酸酯上的氟与硅相互作用并激活Si-O键，从而使二苯甲基甲硅烷基选择性脱甲硅烷基化。在存在仲甲硅烷基醚的情况下，三氟硼酸酯对伯甲硅烷基醚的选择性脱甲硅烷基也成功。