8-epikingiside acetate | 53797-44-7

• 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: 8-epikingiside acetate
• 英文别名: methyl (1S,4aS,8S,8aS)-8-methyl-6-oxo-1-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-1,4a,5,6,8,8a-hexahydropyrano<3,4-c>pyran-4-carboxylate；8-epikingiside tetraacetate；8-Epi-gisid-tetraacetat；methyl (1R,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: 53797-44-7
• 化学式: C₂₅H₃₂O₁₅
• 分子量: 572.52
• InChiKey: UAHVKBKQLXMVPS-HNZAWHDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  185.49
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  methyl (1S,4aS,6RS,8S,8aS)-6-hydroxy-8-hydroxymethyl-1-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-1,4a,5,6,8,8a-hexahydro-pyrano<3,4-c>pyran-4-carboxylate 在 4-二甲氨基吡啶 、 sodium acetate 、 sodium cyanoborohydride 、 pyridinium chlorochromate 作用下， 以 吡啶 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 8-epikingiside acetate
  参考文献：
  名称：

  生物成因关键中间体secologanin的仿生转化：secoiridoid secogalioside的首次合成

  摘要：

  用四氧化氧化secologanin四乙酸酯2得到45％的双环半缩醛3，通过用N-氯代琥珀酰亚胺二甲基硫醚络合物处理，得到的缩水甘油四乙酸缩水甘油酯8的产率为29％，另外还得到了62％的三环缩醛6 。硫醇解8产生了60％的半乳糖苷9。

  DOI：

  10.1016/s0040-4020(01)86082-8

文献信息

• A secoiridoid glucoside from Ligustrum japonicum
  作者：Hiroshi Kuwajima、Katsunori Matsuuchi、Kiyokazu Takaishi、Kenichiro Inoue、Tetsuro Fujita、Hiroyuki Inouye

  DOI：10.1016/s0031-9422(00)97757-4

  日期：——

  Abstract Besides several secoiridoid glucosides including 8-epikingiside, a new secoiridoid glucoside, methyl glucooleoside, was isolated from the ripe berries of Ligustrum japonicum and its structure elucidated.

  摘要 除了8-表皮金苷等多种类环烯醚萜苷外，从女贞子的成熟浆果中分离得到了一种新的类环烯醚萜苷——甲基葡萄糖苷，并阐明了其结构。
• 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.
• KUWAJIMA, HIROSHI;MATSUUCHI, KATSUNORI;TAKAISHI, KIYOKAZU;INOUE, KENICHIR+, PHYTOCHEMISTRY, 28,(1989) N, C. 1409-1411
  作者：KUWAJIMA, HIROSHI、MATSUUCHI, KATSUNORI、TAKAISHI, KIYOKAZU、INOUE, KENICHIR+

  DOI：——

  日期：——
• KIKUCHI, MASAO;YAMAUCHI, YOKO;TAKAHASHI, YUKA;NAGAOKA, ICHIRO;SUGIYAMA, M+, J. PHARM. SOC. JAP., 108,(1988) N 4, 355-360
  作者：KIKUCHI, MASAO、YAMAUCHI, YOKO、TAKAHASHI, YUKA、NAGAOKA, ICHIRO、SUGIYAMA, M+

  DOI：——

  日期：——
• TIETZE, LUTZ F.;HENKE, STEPHAN;BARTELS, CHRISTOPH, TETRAHEDRON, 44,(1988) N 23, C. 7145-7153
  作者：TIETZE, LUTZ F.、HENKE, STEPHAN、BARTELS, CHRISTOPH

  DOI：——

  日期：——