caudatoside A pentaacetate | 477292-66-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: caudatoside A pentaacetate
• 英文别名: methyl (1S,4aS,5S,6R,7S,7aR)-6-acetyloxy-7-methyl-5-[(E)-3-phenylprop-2-enoyl]oxy-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• CAS: 477292-66-3
• 化学式: C₃₆H₄₂O₁₇
• 分子量: 746.719
• InChiKey: ULSLXILQJZFRQD-IFKBELQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  caudatoside A pentaacetate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以51%的产率得到caudatoside A
  参考文献：
  名称：

  Conversion of 5-Deoxypulchelloside I to Caudatoside A

  摘要：

  The iridoid caudatoside A (2) was synthesized in seven steps from the naturally occurring iridoid 5-deoxypulchelloside I (1) using a straightforward series of protection and deprotection procedures to introduce the requisite C-6 cinnamoyl ester.

  DOI：

  10.1021/np0303613
• 作为产物：
  描述：

  6,7:4',6'-di-O-isopropylidene 5-deoxypulchelloside I 在 吡啶 、 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 caudatoside A pentaacetate
  参考文献：
  名称：

  Conversion of 5-Deoxypulchelloside I to Caudatoside A

  摘要：

  The iridoid caudatoside A (2) was synthesized in seven steps from the naturally occurring iridoid 5-deoxypulchelloside I (1) using a straightforward series of protection and deprotection procedures to introduce the requisite C-6 cinnamoyl ester.

  DOI：

  10.1021/np0303613

文献信息

• Caudatosides A−F:  New Iridoid Glucosides from <i>Citharexylum </i><i>c</i><i>audatum</i>
  作者：Sloan Ayers、Albert T. Sneden

  DOI：10.1021/np020211c

  日期：2002.11.1

  Six new iridoid glucosides, caudatosides A-F (2-7), and one known iridoid glucoside, 5-deoxypulchelloside I (1), were isolated from the fruits of Citharexylum caudatum. The structures of these compounds were elucidated by various one- and two-dimensional NMR techniques as well as high-resolution negative-ion ESIMS. Other plant parts were extracted on a small scale, and TLC of these extracts revealed the presence of the same iridoids.