methyl (2S,3R,4S)-4-(1,3-dioxolan-2-ylmethyl)-3-ethenyl-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate | 233661-53-5

• 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: methyl (2S,3R,4S)-4-(1,3-dioxolan-2-ylmethyl)-3-ethenyl-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 233661-53-5
• 化学式: C₄₃H₆₄O₂₂Si
• 分子量: 961.053
• InChiKey: BYCJXYSFNCDJNN-NYUUAXCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  66
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  258
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,4S)-4-(1,3-dioxolan-2-ylmethyl)-3-ethenyl-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate 在 水 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 生成 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：

  N-(3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-piperidine 在 咪唑 、 Cl⁽³⁾HO₄ 、 水 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 methyl (2S,3R,4S)-4-(1,3-dioxolan-2-ylmethyl)-3-ethenyl-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
  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