rhizochalin peracetate | 1189045-35-9

• 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: rhizochalin peracetate
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,26R,27R)-2,27-diacetamido-26-acetyloxy-18-oxooctacosan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1189045-35-9
• 化学式: C₄₈H₈₂N₂O₁₅
• 分子量: 927.183
• InChiKey: OOMYKZXZPDLZEL-OHNWZYSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  65
• 可旋转键数：
  40
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  225
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  甲醇 、 rhizochalin peracetate 、 乙酸酐 在 双氧水 、 三氟乙酸 、 吡啶 作用下， 反应 202.0h， 生成 methyl (9R,10R)-10-acetamido-9-acetyloxyundecanoate 、 [(8R,9R)-9-acetamido-8-acetyloxydecyl] acetate 、 methyl (16R,17R)-17-acetamido-16-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoctadecanoate 、 [(15R,16R)-16-acetamido-15-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyheptadecyl] acetate
  参考文献：
  名称：

  Rhizochalins C and D from the Sponge Rhizochalina incrustata. A Rare threo-Sphingolipid and a Facile Method for Determination of the Carbonyl Position in α,ω-Bifunctionalized Ketosphingolipids

  摘要：

  Rhizochalins C and D (1, 2), new representatives of two-headed glycosphingolipids, were isolated from the sponge Rhizochalina incrustata. Rhizochalin D is an unexpected C-29 homologue of the canonical C-28 dimeric sphingolipid structures. Their structures including absolute configurations were established using spectroscopic data, micromolar-scale Baeyer-Villiger oxidation, and LCMS interpretation of the products. Application of the latter method leads to a revision of the structure of oceanapiside and placement of the keto group at C-18 rather than C-11.

  DOI：

  10.1021/np0704811

文献信息

• Rhizochalins C and D from the Sponge <i>Rhizochalina incrustata.</i> A Rare <i>threo</i>-Sphingolipid and a Facile Method for Determination of the Carbonyl Position in α,ω-Bifunctionalized Ketosphingolipids
  作者：Tatyana N. Makarieva、Pavel S. Dmitrenok、Alexander M. Zakharenko、Vladimir A. Denisenko、Alla G. Guzii、Ronghua Li、Colin K. Skepper、Tadeusz F. Molinski、Valentin A. Stonik

  DOI：10.1021/np0704811

  日期：2007.12.1

  Rhizochalins C and D (1, 2), new representatives of two-headed glycosphingolipids, were isolated from the sponge Rhizochalina incrustata. Rhizochalin D is an unexpected C-29 homologue of the canonical C-28 dimeric sphingolipid structures. Their structures including absolute configurations were established using spectroscopic data, micromolar-scale Baeyer-Villiger oxidation, and LCMS interpretation of the products. Application of the latter method leads to a revision of the structure of oceanapiside and placement of the keto group at C-18 rather than C-11.