N-tert-butoxycarbonyl-o,o'-diiodo-L-tyrosyl-L-allo-threonyl-o,o'-dibromo-L-tyrosine methyl ester | 733054-76-7

• 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-tert-butoxycarbonyl-o,o'-diiodo-L-tyrosyl-L-allo-threonyl-o,o'-dibromo-L-tyrosine methyl ester
• 英文别名: Boc-Tyr(3,5-diI)-aThr-Tyr(3,5-diBr)-OMe；methyl (2S)-3-(3,5-dibromo-4-hydroxyphenyl)-2-[[(2S,3S)-3-hydroxy-2-[[(2S)-3-(4-hydroxy-3,5-diiodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]butanoyl]amino]propanoate
• CAS: 733054-76-7
• 化学式: C₂₈H₃₃Br₂I₂N₃O₉
• 分子量: 969.202
• InChiKey: QOBLIMOGZSFEEL-XSGSXHBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  184
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-o,o'-diiodo-L-tyrosyl-L-allo-threonyl-o,o'-dibromo-L-tyrosine methyl ester 在 palladium on activated charcoal 氢气 、 sodium acetate 、 thallium(III) nitrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 N-tert-butoxycarbonyl-eurypamide D methyl ester
  参考文献：
  名称：

  Total synthesis of eurypamides, marine cyclic-isodityrosines from the Palauan sponge Microciona eurypa

  摘要：

  Total synthesis of eurypamides A, B, and D, 1, 2, and 4, has been successfully accomplished. The Tl(NO3)(3) (TTN) oxidation of the halogenated bisphenols, 14a, 14b, 24, and 43, effected regio-controlled cyclization to provide the corresponding diaryl ethers, 15a, 15b, 25, and 46. This investigation revealed a structural revision of eurypamide A as to possess (2"S,3"R,4"S)-configuration (47), along with the spectral data of pure 2 and 4, which were previously characterized in a mixture. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.062
• 作为产物：
  描述：

  N-叔丁氧羰基-3,5-二碘-L-酪氨酸 、 (S)-2-((2S,3S)-2-Amino-3-hydroxy-butyrylamino)-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester; compound with trifluoro-acetic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以340.4 mg的产率得到N-tert-butoxycarbonyl-o,o'-diiodo-L-tyrosyl-L-allo-threonyl-o,o'-dibromo-L-tyrosine methyl ester
  参考文献：
  名称：

  Total synthesis of eurypamides, marine cyclic-isodityrosines from the Palauan sponge Microciona eurypa

  摘要：

  Total synthesis of eurypamides A, B, and D, 1, 2, and 4, has been successfully accomplished. The Tl(NO3)(3) (TTN) oxidation of the halogenated bisphenols, 14a, 14b, 24, and 43, effected regio-controlled cyclization to provide the corresponding diaryl ethers, 15a, 15b, 25, and 46. This investigation revealed a structural revision of eurypamide A as to possess (2"S,3"R,4"S)-configuration (47), along with the spectral data of pure 2 and 4, which were previously characterized in a mixture. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.062