(4S,5R,6S)-4-[1,3]Dioxolan-2-ylmethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester | 233661-50-2

• 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: (4S,5R,6S)-4-[1,3]Dioxolan-2-ylmethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
• 英文别名: methyl (2S,3R,4S)-4-(1,3-dioxolan-2-ylmethyl)-3-ethenyl-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 233661-50-2
• 化学式: C₂₅H₃₄O₁₄
• 分子量: 558.537
• InChiKey: RORKVZMXJXOAAK-UCSVYGSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-4-[1,3]Dioxolan-2-ylmethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 在 Cl⁽³⁾HO₄ 、 水 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (4S,5R,6S)-4-(2-Oxo-ethyl)-6-[(2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
  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：

  (4S,5R,6S)-6-[(2S,3R,4S,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yloxy]-4-(2-oxo-ethyl)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 在 Amberlite IR 120B 、 四丁基氟化铵 、 溶剂黄146 、 sodium sulfate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (4S,5R,6S)-4-[1,3]Dioxolan-2-ylmethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
  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