(4S)-5c-ethyl-6t-β-D-glucopyranosyloxy-4r-(2-oxo-ethyl)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester | 52530-99-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4S)-5c-ethyl-6t-β-D-glucopyranosyloxy-4r-(2-oxo-ethyl)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
• 英文别名: methyl (2S,3R,4S)-3-ethyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 52530-99-1
• 化学式: C₁₇H₂₆O₁₀
• 分子量: 390.387
• InChiKey: NWFQFCXUBLVAIA-NRZPKYKESA-N

物化性质

• 沸点：
  592.4±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4S)-5c-ethyl-6t-β-D-glucopyranosyloxy-4r-(2-oxo-ethyl)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 生成 ent-17,21α-epoxy-(15βH)-coryn-16-ene-16-carboxylic acid methyl ester
  参考文献：
  名称：

  吲哚生物碱的仿生合成：二氢mancunine

  摘要：

  二氢mancunine（2a），一种拟议的生物合成中间体的模型，已从酒酚苷合成，并按照仿生顺序转化为Corynanthé吲哚生物碱。hirsutine（6b）和二氢corynantheine（6c）也已经合成。

  DOI：

  10.1039/c39740000756

文献信息

• Conversion of secologanin into Corynanthé-type alkaloids
  作者：Richard T. Brown、C. Lyn Chapple

  DOI：10.1039/c3973000886b

  日期：——

  Indole alkaloids of the Corynanthé type have been synthesised from secolognin via 3β-hexahydrode-oxycordifoline, the major steps corresponding to a possible biosynthetic sequence.

  所述的吲哚生物碱柯楠因类型已从secolognin合成经由3 β -hexahydrode-oxycordifoline，对应于可能的生物合成序列中的主要步骤。
• Chemistry of secologanin. Part 5. Graphical analysis of the acidic deglycosylation of vincoside derivatives
  作者：L�szl� K�rolyh�zy、�gnes Luk�ts-Patthy、L�szl� F. Szab�

  DOI：10.1002/(sici)1099-1395(199808/09)11:8/9<622::aid-poc51>3.0.co;2-l

  日期：1998.8

  Acidic hydrolysis and cyclization were studied in vincoside glycosides ('natural' series) and their dihydro derivatives ('dihydro' series) in which either one or both N atoms were free or blocked by an alkyl group. For interpretation of the results, a graph was constructed in which 25 points (actually circles) represent a maximum of 81 aglycone types and 40 arrows indicate 131 possible cyclizations. The reaction matrix of the graph was under thermodynamic control and in most cases afforded the thermodynamically most stable product aglycones. In addition to the deglycosylation, two types of cyclization were observed. In azacyclizations, the preferred nucleophilic site is N-4 over N-1, and the preferred electrophilic site is C-22 in the glycosides, C-21 over C-19 and C-17 in aglycones. In oxacyclizations, the preferred nucleophilic site is O-17 over C-18 and C-21, and the preferred electrophilic site is C-19 over C-21 and C-17 in the 'natural' series, C-21 over C-17 in the 'dihydro' series. In one case, the kinetically favoured aglycone types which had been generated in the reaction mixture were trapped in a subsequent reaction (outside the graph) before thermodynamic equilibrium was attained. With the help of graphical analysis it was possible to justify the formation of the most favourable and actually isolated products and pathways out of a large number of possibilities. (C) 1998 John Wiley & Sons, Ltd.
• Brown; Leonard, Journal of the Indian Chemical Society, 1979, vol. 55, # 11, p. 1092 - 1095
  作者：Brown、Leonard

  DOI：——

  日期：——
• Biomimetic synthesis of indole alkaloids: dihydromancunine
  作者：Richard T. Brown、C. Lyn Chapple、Antonios A. Charalambides

  DOI：10.1039/c39740000756

  日期：——

  Dihydromancunine (2a), a model for a proposed biosynthetic intermediate, has been synthesised from vincoside and converted into Corynanthé indole alkaloids in a biomimetic sequence; hirsutine (6b) and dihydrocorynantheine (6c) have also been synthesised.

  二氢mancunine（2a），一种拟议的生物合成中间体的模型，已从酒酚苷合成，并按照仿生顺序转化为Corynanthé吲哚生物碱。hirsutine（6b）和二氢corynantheine（6c）也已经合成。