5-((S)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-methoxy-3-oxopropyl)-2-methoxyphenylboronic acid | 606139-98-4

• 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: 5-((S)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-methoxy-3-oxopropyl)-2-methoxyphenylboronic acid
• 英文别名: [5-[(2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-methoxy-3-oxopropyl]-2-methoxyphenyl]boronic acid
• CAS: 606139-98-4
• 化学式: C₂₅H₃₃BN₂O₉
• 分子量: 516.356
• InChiKey: SZFXCEQNKOVVGN-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  164
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-((S)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-methoxy-3-oxopropyl)-2-methoxyphenylboronic acid 在 4-二甲氨基吡啶 、 copper diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 以60%的产率得到(9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7(19),14,16,17-hexaene
  参考文献：
  名称：

  Improved Synthesis of L,L-Cycloisodityrosine Subunit of Antitumor Agents Deoxybouvardin and RA-VII

  摘要：

  A facile synthesis of the core cycloisodityrosine 14-membered ring system is detailed from commercially available L-tyrosine through a novel synthetic approach to aryl boronic acid 12 via intramolecular cyclization.

  DOI：

  10.1080/00397910903245166
• 作为产物：
  描述：

  (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 在 sodium periodate 、 ammonium acetate 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以90%的产率得到5-((S)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-methoxy-3-oxopropyl)-2-methoxyphenylboronic acid
  参考文献：
  名称：

  Improved Synthesis of L,L-Cycloisodityrosine Subunit of Antitumor Agents Deoxybouvardin and RA-VII

  摘要：

  A facile synthesis of the core cycloisodityrosine 14-membered ring system is detailed from commercially available L-tyrosine through a novel synthetic approach to aryl boronic acid 12 via intramolecular cyclization.

  DOI：

  10.1080/00397910903245166

文献信息

• Synthesis of l,l-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids
  作者：Yukio Hitotsuyanagi、Hiroshi Ishikawa、Syunsuke Naito、Koichi Takeya

  DOI：10.1016/s0040-4039(03)01390-x

  日期：2003.7

  Two types of cycloisodityrosines, 11 and 13, were synthesized from commercially available chiral tyrosine derivatives through the copper(II) acetate-DMAP-mediated diaryl ether formation of boronotyrosyltyrosines 8 and 10, respectively. (C) 2003 Elsevier Ltd. All rights reserved.
• Improved Synthesis of L,L-Cycloisodityrosine Subunit of Antitumor Agents Deoxybouvardin and RA-VII
  作者：Samir Ghosh、A. Sanjeev Kumar、G. N. Mehta、R. Soundararajan

  DOI：10.1080/00397910903245166

  日期：2010.7.27

  A facile synthesis of the core cycloisodityrosine 14-membered ring system is detailed from commercially available L-tyrosine through a novel synthetic approach to aryl boronic acid 12 via intramolecular cyclization.