N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanyl-L-(4-O-benzyl)-aspartic acid α-tert-butyl ester | 945245-54-5

• 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: N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanyl-L-(4-O-benzyl)-aspartic acid α-tert-butyl ester
• CAS: 945245-54-5
• 化学式: C₄₀H₄₂N₂O₁₀S
• 分子量: 742.847
• InChiKey: VHYLODQKWRYFON-PXLJZGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  174.4
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanyl-L-(4-O-benzyl)-aspartic acid α-tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以73%的产率得到N-(fluorenyl-9-methoxycarboynl)-L-(p-sulfomethyl)phenylalanyl-L-(4-O-benzyl)-aspartic acid
  参考文献：
  名称：

  (p-Sulfomethyl)phenylalanine as a mimic of O-sulfatyl-tyrosine in synthetic partial sequences of P-Selectin glycoprotein ligand 1 (PSGL-1)

  摘要：

  Fmoc-L-(p-sulfomethyl)phenylalanine, a bioisosteric mimic of acid-sensitive O-sulfatyl tyrosine, was synthesized from L-tyrosine according to a novel route. Partial sequences of the recognition site of P-Selectin glycoprotein ligand 1 (PSGL-1), which contain (sulfomethyl) phenylalanine were synthesized on solid-phase. By fragment condensation, a sialyl Lewis(x) peptide conjugate containing a (sulfomethyl)phenylalanine mimic of O-sulfatyl tyrosine was prepared without destruction of the acid-sensitive fucoside bond within the saccharide side chain. Compounds of this type are of interest as sufficiently acid-stable potential inhibitors of P-Selectin in inflammatory processes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.028
• 作为产物：
  描述：

  methyl (2S)-3-[4-(aminomethyl)phenyl]-2-{[(tert-butoxy)carbonyl]amino}propanoate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 sodium sulfite 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanyl-L-(4-O-benzyl)-aspartic acid α-tert-butyl ester
  参考文献：
  名称：

  (p-Sulfomethyl)phenylalanine as a mimic of O-sulfatyl-tyrosine in synthetic partial sequences of P-Selectin glycoprotein ligand 1 (PSGL-1)

  摘要：

  Fmoc-L-(p-sulfomethyl)phenylalanine, a bioisosteric mimic of acid-sensitive O-sulfatyl tyrosine, was synthesized from L-tyrosine according to a novel route. Partial sequences of the recognition site of P-Selectin glycoprotein ligand 1 (PSGL-1), which contain (sulfomethyl) phenylalanine were synthesized on solid-phase. By fragment condensation, a sialyl Lewis(x) peptide conjugate containing a (sulfomethyl)phenylalanine mimic of O-sulfatyl tyrosine was prepared without destruction of the acid-sensitive fucoside bond within the saccharide side chain. Compounds of this type are of interest as sufficiently acid-stable potential inhibitors of P-Selectin in inflammatory processes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.028