21,22-dihydroxyonnamide A₃ | 1080024-55-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 21,22-dihydroxyonnamide A₃
• 英文别名: (2S)-2-[[(2E,4E,6S,7S,11R)-12-[(4S,4aS,6R,8S,8aR)-4-[[(2S)-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetyl]amino]-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-6-yl]-6,7,11-trihydroxydodeca-2,4-dienoyl]amino]-5-(diaminomethylideneamino)pentanoic acid
• CAS: 1080024-55-0
• 化学式: C₃₉H₆₅N₅O₁₄
• 分子量: 827.97
• InChiKey: XAFCNBUPFXGRRK-FAOVDWTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  58
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  296
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  21,22-dihydroxyonnamide A₃ 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 isopropylidene derivative of 21,22-dihydroxyonnamide A₃
  参考文献：
  名称：

  Structure elucidation of 21,22-dihydroxyonnamides A1–A4 from the marine sponge Theonella swinhoei: an empirical rule to assign the relative stereochemistry of linear 1,5-diols

  摘要：

  A polar cytotoxic fraction of the marine sponge Theonella swinhoei was analyzed to be a mixture of four isomeric compounds, 21,22-dihydroxyonnamides A(1), A(2), A(3), and A(4). They were separated after conversion to the isopropyridene derivatives. The structures of the 21S,22S- and 21R,22R-isomers were determined by comparison of their spectral data with those prepared from onnamide A by asymmetric dihydroxylation. During the analysis of NMR data of these derivatives, an empirical rule was implied to assign the relative stereochemistry of linear 1,5-diol. This rule was applied to assign the stereochemistry of the remaining congeners. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.057
• 作为产物：
  描述：

  2-[[(2E,4E,6E,11R)-12-[(4aS,6R,8S,8aR)-4-[[(2S)-2-羟基-2-[(2R,5R,6R)-2-甲氧基-5,6-二甲基-4-亚甲基-四氢吡喃-2-基]乙酰]氨基]-8-甲氧基-7,7-二甲基-4a,6,8,8a-四氢-4H-吡喃并[5,6-d][1,3]二恶英-6-基]-11-羟基-十二碳-2,4,6-三烯酰基]氨基]-5-(二氨基亚甲基氨基)戊酸 在 AD-mix-α 作用下， 生成 21,22-dihydroxyonnamide A₃
  参考文献：
  名称：

  Structure elucidation of 21,22-dihydroxyonnamides A1–A4 from the marine sponge Theonella swinhoei: an empirical rule to assign the relative stereochemistry of linear 1,5-diols

  摘要：

  A polar cytotoxic fraction of the marine sponge Theonella swinhoei was analyzed to be a mixture of four isomeric compounds, 21,22-dihydroxyonnamides A(1), A(2), A(3), and A(4). They were separated after conversion to the isopropyridene derivatives. The structures of the 21S,22S- and 21R,22R-isomers were determined by comparison of their spectral data with those prepared from onnamide A by asymmetric dihydroxylation. During the analysis of NMR data of these derivatives, an empirical rule was implied to assign the relative stereochemistry of linear 1,5-diol. This rule was applied to assign the stereochemistry of the remaining congeners. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.057