methyl (S)-2-((tert-butoxycarbonyl)amino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate | 1241902-82-8

• 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: methyl (S)-2-((tert-butoxycarbonyl)amino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate
• CAS: 1241902-82-8
• 化学式: C₁₇H₃₂BNO₆
• 分子量: 357.255
• InChiKey: ZIJDETNAEGECMV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-((tert-butoxycarbonyl)amino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate 在 甲醇 、 水 、 potassium carbonate 作用下， 生成 [(4S)-5-methoxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentyl]boronic acid
  参考文献：
  名称：

  Probe molecule equipped with boronic acid moiety as a reversible cross-linking group improves its binding affinity

  摘要：

  Syntheses of biotinylated probe molecules of L-glutathione (GSH) equipped with boronic acid moiety and evaluation of their binding affinities against glutathione-S-transferase (GST) were described. It revealed that the presence of boronic acid moiety in an appropriate position enhances binding affinity of GSH probe toward GST probably by forming a reversible cross-link. Among prepared, the boronate-containing probe 8b exhibited the highest recovering ability of GST from Escherichia coli cell lysate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.052
• 作为产物：
  描述：

  N-Boc-L-烯丙基甘氨酸甲酯 、 频那醇硼烷 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到methyl (S)-2-((tert-butoxycarbonyl)amino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate
  参考文献：
  名称：

  Probe molecule equipped with boronic acid moiety as a reversible cross-linking group improves its binding affinity

  摘要：

  Syntheses of biotinylated probe molecules of L-glutathione (GSH) equipped with boronic acid moiety and evaluation of their binding affinities against glutathione-S-transferase (GST) were described. It revealed that the presence of boronic acid moiety in an appropriate position enhances binding affinity of GSH probe toward GST probably by forming a reversible cross-link. Among prepared, the boronate-containing probe 8b exhibited the highest recovering ability of GST from Escherichia coli cell lysate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.052

文献信息

• Synthesis, Structure, and Function of PCP Pincer Transition-Metal-Complex-Bound Norvaline Derivatives
  作者：Hikaru Takaya、Masaharu Nakamura、Takashi Iwaya、Kazuki Ogata、Katsuhiro Isozaki、Tomoya Yokoi、Ryota Yoshida、Nobuhiro Yasuda、Hirofumi Seike、Toshio Takenaka

  DOI：10.1055/s-0033-1339473

  日期：——

  A PCP pincer palladium-complex-bound norvaline, Boc-l-[Pd]Nva-OMe, was synthesized and fully characterized by NMR, FT-ICR-MS, and X-ray crystallography. Selective N- and C-terminus transformations of Boc-l-[Pd]Nva-OMe were performed by conventional deprotection-condensation procedures to afford lipophilic palladium-bound norvaline derivatives without metal detachment. The N-/C-bisfunctionalized palladium-bound norvaline showed self-assembly properties, as evidenced by supramolecular gel formation. The catalytic activity of the supramolecular gel was assessed in the 1,4-conjugate addition of phenylboronic acid.