kungiside tetraacetate | 25406-70-6

• 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: kungiside tetraacetate
• 英文别名: tetraacetylkingiside；Kingisid-tetraacetat；Kingiridtetraacetat；Kingisidtetraacetat；methyl (1S,4aS,8S,8aS)-1-methyl-3-oxo-8-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4,4a,8,8a-tetrahydro-1H-pyrano[3,4-c]pyran-5-carboxylate
• CAS: 25406-70-6
• 化学式: C₂₅H₃₂O₁₅
• 分子量: 572.52
• InChiKey: UAHVKBKQLXMVPS-UHNBPNNQSA-N

物化性质

• 沸点：
  650.7±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  kungiside tetraacetate 生成 (-)-xylomollin
  参考文献：
  名称：

  木糖醇的仿生化学

  摘要：

  Kingiside配糖苷（2b）对其CH（3,4）烯醇醚双键进行立体选择性的CH 3 OH加成反应，得到木糖醇（1）的C（1,3,9）非对映异构体，一种具有昆虫拒食性的赛多孢子苷元。 。

  DOI：

  10.1016/s0040-4039(00)71372-4
• 作为产物：
  描述：

  10-deoxygeniposide tetraacetate 在 sodium tetrahydroborate 、 高氯酸 、 jones' reagent 、 2-甲基-4-氯苯氧乙酸 作用下， 以 1,4-二氧六环 、 乙醚 、 丙酮 、 苯 为溶剂， 反应 9.83h， 生成 kungiside tetraacetate
  参考文献：
  名称：

  Biosynthesis of iridoids in Syringa and Fraxinus: Secoiridoid precursors

  摘要：

  Several deuterium-labelled secoiridoids have been prepared and tested as possible precursors for the iridoids in Fraxinus excelsior, Syringa josikaea and S. vulgaris. Oleoside Ii-methyl ester was an efficient precursor for the oleosides, whereas secologanin-type iridoids gave only significant incorporation in 5. josikaea. In this plant low incorporations into the oleosides were also seen for kingiside and 8-epi-kingiside. The major pathway to the oleosides therefore seems to proceed via a direct ring fission of ketologanin to oleoside 11-methyl ester. A Baeyer-Villiger-like mechanism which explains the different compounds found in the plants is proposed, and the taxonomy of the Oleaceae is discussed. Due to the unique presence of the usual pathway leading to secologanin and its congeners in Fontanesia, the Oleaceae is considered to be a member of the Gentiananae rather than Scrophulariales/Lamianae.

  DOI：

  10.1016/0031-9422(95)00211-o

文献信息

• Kingiside and derivative fromGentiana pyrenaica
  作者：Julian Garcia、Emmanuel Mpondo Mpondo、Mourad Kaouadji

  DOI：10.1016/0031-9422(90)80214-2

  日期：1990.1

  Abstract From the aerial part of Gentiana pyrenaica , 6′-vanilloyl kingiside, a new secoiridoid glucoside was isolated along with the known kingiside and 7-demethyl alpigenoside. The latter was found to be an artifact formed from kingiside in the isolation procedure. Their structures were elucidated on the basis of spectroscopic studies.

  摘要 从龙胆的地上部分，6'-香草酰金苷，与已知的金苷和7-去甲基山金苷苷一起分离出一种新的类环烯醚萜苷。后者被发现是在隔离过程中由金苷形成的人工制品。在光谱研究的基础上阐明了它们的结构。
• 10.1002/(sici)1099-0690(200004)2000:8<1623::aid-ejoc1623<3.0.co;2-y
  作者：Weinges, Klaus、Schick, Hartmut、Ziegler, Hans Juergen

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1623::aid-ejoc1623<3.0.co;2-y

  日期：——
• GARCIA, JULIAN;MPONDO, EMMANUEL;KAOUADH, MOURAD, PHYTOCHEMISTRY, 29,(1990) N0, C. 3353-3355
  作者：GARCIA, JULIAN、MPONDO, EMMANUEL、KAOUADH, MOURAD

  DOI：——

  日期：——
• Biosynthesis of iridoids in Syringa and Fraxinus: Secoiridoid precursors
  作者：Søren Damtoft、Henrik Franzyk、Søren Rosendal Jensen

  DOI：10.1016/0031-9422(95)00211-o

  日期：1995.10

  Several deuterium-labelled secoiridoids have been prepared and tested as possible precursors for the iridoids in Fraxinus excelsior, Syringa josikaea and S. vulgaris. Oleoside Ii-methyl ester was an efficient precursor for the oleosides, whereas secologanin-type iridoids gave only significant incorporation in 5. josikaea. In this plant low incorporations into the oleosides were also seen for kingiside and 8-epi-kingiside. The major pathway to the oleosides therefore seems to proceed via a direct ring fission of ketologanin to oleoside 11-methyl ester. A Baeyer-Villiger-like mechanism which explains the different compounds found in the plants is proposed, and the taxonomy of the Oleaceae is discussed. Due to the unique presence of the usual pathway leading to secologanin and its congeners in Fontanesia, the Oleaceae is considered to be a member of the Gentiananae rather than Scrophulariales/Lamianae.
• Biomimetic chemistry of xylomollin
  作者：Saifunnissa B. Hassam、C. Richard Hutchinson

  DOI：10.1016/s0040-4039(00)71372-4

  日期：——

  Kingiside aglucon (2b) undergoes stereoselective addition of CH3OH to its C(3,4) enol ether double bond to give a C(1,3,9) diastereomer of xylomollin (1), a secoiridoid aglucon that has insect antifeedant properties.

  Kingiside配糖苷（2b）对其CH（3,4）烯醇醚双键进行立体选择性的CH 3 OH加成反应，得到木糖醇（1）的C（1,3,9）非对映异构体，一种具有昆虫拒食性的赛多孢子苷元。 。