2-((2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-maltosyl)oxy)benzaldehyde | 147568-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-maltosyl)oxy)benzaldehyde
• 英文别名: 2-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-D-maltosyloxy)benzaldehyde；2-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-D-maltosyloxy)benzaldehyde；2-(2,3,6,2',3',4',6'-heptaacetyl-β-D-maltosyl)benzaldehyde；Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(b)-O-Ph(2-For)；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-(2-formylphenoxy)-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 147568-04-5
• 化学式: C₃₃H₄₀O₁₉
• 分子量: 740.669
• InChiKey: HMUPADIECNAWJK-RCQOQWBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-((2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-maltosyl)oxy)benzaldehyde 在 potassium permanganate 、 水 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以91.1%的产率得到2-[(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-D-maltosyl)oxy]benzoic acid
  参考文献：
  名称：

  Synthesis of Glycosylated Chrysin Derivatives Via Ester Linkers

  摘要：

  一系列糖基化的黄酮衍生物已通过简单的工艺和温和的反应条件合成，产率良好。通过每个酯链接引入了六种不同的糖基。

  DOI：

  10.1007/s10600-016-1721-5
• 作为产物：
  描述：

  麦芽糖 在 高氯酸 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 2-((2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-maltosyl)oxy)benzaldehyde
  参考文献：
  名称：

  Synthesis of Glycosylated Chrysin Derivatives Via Ester Linkers

  摘要：

  一系列糖基化的黄酮衍生物已通过简单的工艺和温和的反应条件合成，产率良好。通过每个酯链接引入了六种不同的糖基。

  DOI：

  10.1007/s10600-016-1721-5

文献信息

• Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy
  作者：Khalid Driaf、Robert Granet、Pierre krausz、Mourad Kaouadji、Bernard Verneuil、François Thomasson、Albert José Chulia、Marenglen Spiro、Jean-Claude Biais、Gérard Bolbach

  DOI：10.1139/v96-172

  日期：1996.8.1

  Trisalkylpyridinium porphyrins substituted by one glycosyl (glucosyl, maltosyl, and lactosyl) moiety have been prepared in acceptable yields. These glycosylated cationic porphyrins have been synthesized from pyrrole condensed with 4-pyridinecarboxaldehyde, and suitable ortho- or para peracetylglycosyloxybenzaldehyde derivatives in refluxing propionic acid –Ac₂O followed by action of alkyliodide in DMF. Deprotection of the glycosylated moieties led to a new class of representative glycosylated porphyrins. Key words: porphyrins, cationic, glycosylated; phototherapy, cancer.

  一种糖基（葡萄糖基、麦芽糖基和乳糖基）取代的三烷基吡啶卟啉已经在可接受的产率下制备。这些糖基化阳离子卟啉是从吡咯与4-吡啶甲醛、适当的邻位或对位过乙酰基糖基羟基苯甲醛衍生物在丙酸-乙酸酐回流中反应，然后在DMF中作用烷基碘化物合成的。去保护糖基后得到了一类新的代表性糖基化卟啉。关键词：卟啉、阳离子、糖基化；光疗法、癌症。
• Glycoconjugated porphyrins. 2. Synthesis of sterically constrained polyglycosylated compounds derived from tetraphenylporphyrins
  作者：Philippe Maillard、Jean Luc Guerquin-Kern、Christiane Huel、Michel Momenteau

  DOI：10.1021/jo00062a020

  日期：1993.5

  A variety of glycoconjugated porphyrins has been synthesized by Lindsey's method from pyrrole and o-acetylglycosylated benzaldehyde precursors. Deprotection of glucose and maltose moieties allows the production of derivatives which had a good solubility in neutral aqueous solution and covered a range of amphiphilic character. The structure in solution of these new compounds was studied by H-1 NMR analysis. A study of the complexation characteristics of their zinc derivatives shows low values of affinity constants which are dependent on the steric hindrance of both faces of the porphyrin macrocycle. The present strategy should prove applicable to the synthesis of other glycoconjugated tetrapyrrolic compounds.
• Synthesis and biological evaluation of glycosylated psoralen derivatives
  作者：Chao-Yue Chen、Jian-Guo Sun、Fei-Yan Liu、Kwok-Pui Fung、Ping Wu、Zhi-Zhen Huang

  DOI：10.1016/j.tet.2012.01.090

  日期：2012.3

  A novel route for the efficient synthesis of a target psoralen moiety, 4,4'-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photoinduced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. (C) 2012 Elsevier Ltd. All rights reserved.