(4aS,5R,6S)-3-Methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-5-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one | 233661-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,5R,6S)-3-Methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-5-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one
• 英文别名: (4aS,5R,6S)-5-ethenyl-3-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one
• CAS: 233661-57-9
• 化学式: C₂₃H₃₄O₁₅
• 分子量: 550.514
• InChiKey: BAAQSSCAXJPWIS-PCEZEFBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  223
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-(2-氨基乙基)吲哚 、 (4aS,5R,6S)-3-Methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-5-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one 以 水 、 溶剂黄146 为溶剂， 以24%的产率得到hunterioside
  参考文献：
  名称：

  First synthesis of hunterioside, a novel disaccharide carrying monoterpenoid indole alkaloid, by assembly of three components, tryptamine, secologanin, and a newly-developed glucosyl donor

  摘要：

  The novel structure of hunterioside, the first example of monoterpenoid indole alkaloids carrying a disaccharide, was confirmed by chemical synthesis starting from tryptamine, secologanin, and a newly-developed gulucosyl donor, which selectively gives alpha-gluco type glycosidic linkage in the reaction with a secologanin derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00928-4
• 作为产物：
  描述：

  开联番木鳖苷 在 吡啶 、 4-二甲氨基吡啶 、 Cl⁽³⁾HO₄ 、 Amberlite IR 120B 、 四丁基氟化铵 、 水 、 potassium carbonate 、 溶剂黄146 、 sodium sulfate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (4aS,5R,6S)-3-Methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-5-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one
  参考文献：
  名称：

  First synthesis of hunterioside, a novel disaccharide carrying monoterpenoid indole alkaloid, by assembly of three components, tryptamine, secologanin, and a newly-developed glucosyl donor

  摘要：

  The novel structure of hunterioside, the first example of monoterpenoid indole alkaloids carrying a disaccharide, was confirmed by chemical synthesis starting from tryptamine, secologanin, and a newly-developed gulucosyl donor, which selectively gives alpha-gluco type glycosidic linkage in the reaction with a secologanin derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00928-4

文献信息

• First synthesis of hunterioside, a novel disaccharide carrying monoterpenoid indole alkaloid, by assembly of three components, tryptamine, secologanin, and a newly-developed glucosyl donor
  作者：Osamu Ohmori、Hiromitsu Takayama、Norio Aimi

  DOI：10.1016/s0040-4039(99)00928-4

  日期：1999.7

  The novel structure of hunterioside, the first example of monoterpenoid indole alkaloids carrying a disaccharide, was confirmed by chemical synthesis starting from tryptamine, secologanin, and a newly-developed gulucosyl donor, which selectively gives alpha-gluco type glycosidic linkage in the reaction with a secologanin derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.