3,5-dimethoxy-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzaldehyde | 117685-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-dimethoxy-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzaldehyde
• 英文别名: 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzaldehyde；O-(Tetra-O-acetyl-β-D-glucopyranosyl)-syringaaldehyd；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-formyl-2,6-dimethoxyphenoxy)oxan-2-yl]methyl acetate
• CAS: 117685-21-9
• 化学式: C₂₃H₂₈O₁₃
• 分子量: 512.468
• InChiKey: QPLSZBIRIYWVKG-IFPLKCGESA-N

物化性质

• 熔点：
  151-153 °C
• 沸点：
  592.0±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  159.19
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxy-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzaldehyde 在 甲醇 、 sodium tetrahydroborate 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  WO2023/102659

  摘要：

  公开号：
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 氢溴酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 15.0h， 生成 3,5-dimethoxy-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzaldehyde
  参考文献：
  名称：

  Coniferin and Derivatives: a Fast and Easy Synthesis via the Aldehyde Series Using Phase-Transfer Catalysis

  摘要：

  在温和条件下，苯丙素以良好的收率（从香草醛出发为56%）合成。通过一锅反应将糖苷化反应与维蒂格反应耦合，生成了香豆醛四-O-乙酰糖苷，可以通过氢化钠轻易还原成四-O-乙酰苯丙素。类似的步骤也用于合成杉木苷和4-香豆醇的糖苷。

  DOI：

  10.1055/s-1998-2009

文献信息

• New syntheses of plant aryl glycosides as potential gene inducers
  作者：Didier Delay、Francis Delmotte

  DOI：10.1016/0008-6215(90)84294-5

  日期：1990.5

  Abstract Aryl β- d -glycopyranosides have been synthesized by coupling acetovanillone (4-hydroxy-3-methoxyacetophenone) with d -glucose, d -galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with d -glucose and d -galactose; syringaldehyde (3-methoxyvanillin) with d -glucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with d -glucose. The Mauthner's procedure

  摘要通过将乙酰香草醛（4-羟基-3-甲氧基苯乙酮）与D-葡萄糖href=https://www.molaid.com/MS_9248 target="_blank">葡萄糖，d-半乳糖和麦芽糖偶联，合成了芳基β-d-吡喃葡萄糖苷。具有D-葡萄糖href=https://www.molaid.com/MS_9248 target="_blank">葡萄糖和d-半乳糖的乙酰丁香酮（4-羟基-3,5-二甲氧基苯乙酮）；带有D-葡萄糖的丁香醛（3-甲氧基香兰素）; 和具有D-葡萄糖href=https://www.molaid.com/MS_9248 target="_blank">葡萄糖的丁香酸（4-羟基-3,5-二甲氧基苯甲酸）。使用在丙酮水溶液中的过乙酰化的糖基溴化物和酚盐的Mauthner方法，得到了乙酰化的β-d-糖苷，将其脱乙酰化。
• First synthesis of (1,2-13C2)-monolignol glucosides
  作者：Vickram Beejmohun、Eric Grand、François Mesnard、Marc-André Fliniaux、José Kovensky

  DOI：10.1016/j.tetlet.2004.09.126

  日期：2004.11

  The monolignol glucosides (1,2-13C2)-p-glucocoumaryl alcohol, (1,2-13C2)-coniferin and (1,2-13C2)-syringin, and the glucosides of (1,2-13C2)-p-coumaric, (1,2-13C2)-ferulic and (1,2-13C2)-sinapic acids were synthesized by condensation of the corresponding aldehydes with (1,2,3-13C3)-malonic acid. The free acids were converted to the acyl chlorides prior to their reduction to alcohols.

  的木质素单体糖苷（1,2- 13 Ç 2） - p -glucocoumaryl醇，（1,2- 13 Ç 2）-coniferin和（1,2- 13 Ç 2）-syringin，和的葡糖苷（1,2 - 13 ç 2） - p香豆，（1,2- 13 ç 2）-ferulic和（1,2- 13 ç 2）-sinapic酸通过用相应的醛的缩合合成（1,2,3- 13 C 3）-丙二酸。在将游离酸还原为醇之前，先将其转化为酰氯。
• Synthesis and structure–activity relationship studies of cytotoxic cinnamic alcohol derivatives
  作者：Hong-Bin Zou、Liang Zhang、Lei-Xiang Yang、Liu-Qing Yang、Yu Zhao、Yong-Ping Yu、Joachim Stöckigt

  DOI：10.1080/14786410902830175

  日期：2011.2

  Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)-6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC50 values of 0.4 and 0.5 mu M, respectively. The structure-activity relationships of the derivatives are discussed.
• Mauthner, Journal fur praktische Chemie (Leipzig 1954), 1930, vol. <2> 124, p. 313,316
  作者：Mauthner

  DOI：——

  日期：——
• Palladium-Catalyzed Stereoconvergent Formylation of (<i>E</i>/<i>Z</i>)-β-Bromo-β-fluorostyrenes: Straightforward Access to (<i>Z</i>)-α-Fluorocinnamic Aldehydes and (<i>Z</i>)-β-Fluorocinnamic Alcohols
  作者：Rajae Zemmouri、Mohammed Kajjout、Yves Castanet、Said Eddarir、Christian Rolando

  DOI：10.1021/jo200798h

  日期：2011.10.7

  We report here the stereoconvergent formylation of (E/Z)-beta-bromo-beta-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-alpha-fluorocinnamaldehydes in good yields. The reaction was extended to styrenes bearing electro-attracting or electro-donating groups. The obtained alpha-fluoroaldehydes were smoothly reduced to the corresponding (Z)-beta-fluorocinnamic alcohol by NaBH4. The reaction could be performed on functionalized substrates as demonstrated by the access to the glucoside of beta-fluoroconiferyl alcohol, (Z)-beta-fluoroconiferin, a strong inhibitor of lignin polymerization.