4-[di-(tert-butyl)phosphonomethyl]phenyl boronic acid | 1009641-03-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 4-[di-(tert-butyl)phosphonomethyl]phenyl boronic acid
• 英文别名: [4-[Bis[(2-methylpropan-2-yl)oxy]phosphorylmethyl]phenyl]boronic acid
• CAS: 1009641-03-5
• 化学式: C₁₅H₂₆BO₅P
• 分子量: 328.153
• InChiKey: VYKWKWCZPDBUTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[di-(tert-butyl)phosphonomethyl]phenyl boronic acid 、 (R)-(+)-benzyl-2-benzamido-3-bromopropanoate 在 bis(1,5-cycloctadiene)Ni⁽⁰⁾ potassium tert-butylate 作用下， 以 仲丁醇 为溶剂， 反应 5.25h， 以85%的产率得到L-N_α-benzoyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine
  参考文献：
  名称：

  A highly efficient route to enantiomerically pure l-N-Bz-Pmp(t-Bu)2-OH and incorporation into a peptide-based protein tyrosine phosphatase inhibitor

  摘要：

  Phosphonomethyl phenylalanine (Pmp), a nonhydrolyzable mimic of phosphotyrosine, is an important building block in the development of peptide-based PTP inhibitors. We have designed a novel, efficient synthesis of N-Bz-Pmp(t-Bu)(2)-OH. A Pmp-containing peptide based on a known biological substrate of the tyrosine phosphatase CD45 (Ac-TEGQ-Pmp-QPQP-NH2) inhibits CD45 with an IC50 value of approximately 100 mu M with virtually no inhibition of TCPTP up to concentrations of 120 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.056
• 作为产物：
  描述：

  di-tert-butyl p-bromobenzylphosphonate 在 正丁基锂 、 硼酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到4-[di-(tert-butyl)phosphonomethyl]phenyl boronic acid
  参考文献：
  名称：

  A highly efficient route to enantiomerically pure l-N-Bz-Pmp(t-Bu)2-OH and incorporation into a peptide-based protein tyrosine phosphatase inhibitor

  摘要：

  Phosphonomethyl phenylalanine (Pmp), a nonhydrolyzable mimic of phosphotyrosine, is an important building block in the development of peptide-based PTP inhibitors. We have designed a novel, efficient synthesis of N-Bz-Pmp(t-Bu)(2)-OH. A Pmp-containing peptide based on a known biological substrate of the tyrosine phosphatase CD45 (Ac-TEGQ-Pmp-QPQP-NH2) inhibits CD45 with an IC50 value of approximately 100 mu M with virtually no inhibition of TCPTP up to concentrations of 120 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.056

文献信息

• A highly efficient route to enantiomerically pure l-N-Bz-Pmp(t-Bu)2-OH and incorporation into a peptide-based protein tyrosine phosphatase inhibitor
  作者：Caitlin E. Hubbard、Amy M. Barrios

  DOI：10.1016/j.bmcl.2007.11.056

  日期：2008.1

  Phosphonomethyl phenylalanine (Pmp), a nonhydrolyzable mimic of phosphotyrosine, is an important building block in the development of peptide-based PTP inhibitors. We have designed a novel, efficient synthesis of N-Bz-Pmp(t-Bu)(2)-OH. A Pmp-containing peptide based on a known biological substrate of the tyrosine phosphatase CD45 (Ac-TEGQ-Pmp-QPQP-NH2) inhibits CD45 with an IC50 value of approximately 100 mu M with virtually no inhibition of TCPTP up to concentrations of 120 mu M. (c) 2007 Elsevier Ltd. All rights reserved.