(S)-2-Benzyloxycarbonylamino-3-[4-hydroxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester | 600737-80-2

• 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: (S)-2-Benzyloxycarbonylamino-3-[4-hydroxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester
• 英文别名: benzyl (2S)-3-[4-hydroxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 600737-80-2
• 化学式: C₃₀H₃₄BNO₇
• 分子量: 531.413
• InChiKey: ZREOSHIGKQPWKZ-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzyl (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate 、 (S)-2-Benzyloxycarbonylamino-3-[4-hydroxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以29%的产率得到(S)-2-Benzyloxycarbonylamino-3-[5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-6,2'-dihydroxy-biphenyl-3-yl]-propionic acid benzyl ester
  参考文献：
  名称：

  A convenient preparation of dityrosine via Miyaura borylation–Suzuki coupling of iodotyrosine derivatives

  摘要：

  Dityrosine has been prepared from 3-iodo-L-tyrosine derivatives by sequential Miyaura borylation and Suzuki coupling reactions. A tandem borylation-coupling protocol results in improved yields of the dityrosine derivatives. Suitable protecting group strategies are employed to allow for global deprotection as the final step. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01081-5
• 作为产物：
  描述：

  N-(苄氧羰基)-L-酪氨酸苄酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 碘 、 potassium acetate 、 silver sulfate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (S)-2-Benzyloxycarbonylamino-3-[4-hydroxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester
  参考文献：
  名称：

  A convenient preparation of dityrosine via Miyaura borylation–Suzuki coupling of iodotyrosine derivatives

  摘要：

  Dityrosine has been prepared from 3-iodo-L-tyrosine derivatives by sequential Miyaura borylation and Suzuki coupling reactions. A tandem borylation-coupling protocol results in improved yields of the dityrosine derivatives. Suitable protecting group strategies are employed to allow for global deprotection as the final step. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01081-5

文献信息

• A convenient preparation of dityrosine via Miyaura borylation–Suzuki coupling of iodotyrosine derivatives
  作者：Craig A. Hutton、Ojia Skaff

  DOI：10.1016/s0040-4039(03)01081-5

  日期：2003.6

  Dityrosine has been prepared from 3-iodo-L-tyrosine derivatives by sequential Miyaura borylation and Suzuki coupling reactions. A tandem borylation-coupling protocol results in improved yields of the dityrosine derivatives. Suitable protecting group strategies are employed to allow for global deprotection as the final step. (C) 2003 Elsevier Science Ltd. All rights reserved.