(3''S,4''R)-eurypamide A | 622379-03-7

• 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: (3''S,4''R)-eurypamide A
• 英文别名: (9S,12S,15S)-9-amino-12-[(1S,2R)-3-(diaminomethylideneamino)-1,2-dihydroxypropyl]-4-hydroxy-10,13-dioxo-2-oxa-11,14-diazatricyclo[15.2.2.13,7]docosa-1(19),3,5,7(22),17,20-hexaene-15-carboxylic acid
• CAS: 622379-03-7
• 化学式: C₂₄H₃₀N₆O₈
• 分子量: 530.538
• InChiKey: WGXANKDMVJQLAR-OVWALXMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  256
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酰丙酮 、 (3''S,4''R)-eurypamide A 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 以71%的产率得到(9S,12S,15S)-9-Amino-12-[(1S,2R)-3-(4,6-dimethyl-pyrimidin-2-ylamino)-1,2-dihydroxy-propyl]-4-hydroxy-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-15-carboxylic acid
  参考文献：
  名称：

  Eurypamide A, a cyclic tripeptide from the Palauan sponge Microciona eurypa

  摘要：

  DOI：

  10.1016/s0040-4020(98)00617-6
• 作为产物：
  描述：

  N-叔丁氧羰基-3,5-二碘-L-酪氨酸 在 palladium on activated charcoal sodium hydroxide 、 四丁基氟化铵 、 水 、 氢气 、 sodium acetate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 thallium(III) nitrate 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (3''S,4''R)-eurypamide A
  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

文献信息

• Synthesis and structural revision of eurypamides isolated from the Palauan sponge Microciona eurypa
  作者：Miyuki Ito、Maki Yamanaka、Noriki Kutsumura、Shigeru Nishiyama

  DOI：10.1016/j.tetlet.2003.08.105

  日期：2003.10

  Eurypamides A and B, 1 and 2, were successfully synthesized by employing Tl(NO3)(3) (TTN) oxidation of the corresponding halogenated phenols, 9, 16, and 26. This investigation revealed that the dihydroxyarginine residue of 1 should be revised to possess (2S,3R,4S)-configuration. In addition, the synthesis of 2 provided a pure sample, which was previously characterized in a mixture. (C) 2003 Elsevier Ltd. All rights reserved.
• Total synthesis of eurypamides, marine cyclic-isodityrosines from the Palauan sponge Microciona eurypa
  作者：Miyuki Ito、Maki Yamanaka、Noriki Kutsumura、Shigeru Nishiyama

  DOI：10.1016/j.tet.2004.04.062

  日期：2004.6

  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.
• Eurypamide A, a cyclic tripeptide from the Palauan sponge Microciona eurypa
  作者：M.Venkata Rami Reddy、Mary Kay Harper、D.John Faulkner

  DOI：10.1016/s0040-4020(98)00617-6

  日期：1998.9