N-tert-butoxycarbonyl-eurypamide D methyl ester | 733054-78-9

• 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-eurypamide D methyl ester
• 英文别名: methyl (9S,12S,15S)-4-hydroxy-12-[(1S)-1-hydroxyethyl]-9-[(2-methylpropan-2-yl)oxycarbonylamino]-10,13-dioxo-2-oxa-11,14-diazatricyclo[15.2.2.13,7]docosa-1(19),3,5,7(22),17,20-hexaene-15-carboxylate
• CAS: 733054-78-9
• 化学式: C₂₈H₃₅N₃O₉
• 分子量: 557.601
• InChiKey: GZKYRSIDOOVWED-AEEVCGNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  173
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-eurypamide D methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (9S,12S,15S)-9-tert-Butoxycarbonylamino-4-hydroxy-12-((S)-1-hydroxy-ethyl)-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-15-carboxylic acid
  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-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

文献信息

• 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.