2-hydroxy-3,4-dimethoxy-5-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]benzaldehyde | 1585169-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3,4-dimethoxy-5-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]benzaldehyde
• CAS: 1585169-38-5
• 化学式: C₄₃H₄₄O₉
• 分子量: 704.817
• InChiKey: JIHONYMJMTYGLM-VYKHTLOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3,4-dimethoxy-5-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]benzaldehyde 在 sodium chlorite 、 草酰氯 、 氨基磺酸 、 sodium hexamethyldisilazane 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 18.41h， 生成 3,4-dimethoxy-2-phenylmethoxy-5-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]benzoyl chloride
  参考文献：
  名称：

  Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties

  摘要：

  The 3,3'-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3'-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 mu M, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.

  DOI：

  10.1021/ol500725e
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟化硼乙醚 、 异丙基氯化镁 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 环己烷 、 乙腈 为溶剂， 反应 4.25h， 生成 2-hydroxy-3,4-dimethoxy-5-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]benzaldehyde
  参考文献：
  名称：

  Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties

  摘要：

  The 3,3'-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3'-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 mu M, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.

  DOI：

  10.1021/ol500725e

文献信息

• Synthesis of 3,3′-Di-<i>O</i>-methyl Ardimerin and Exploration of Its DNA Binding Properties
  作者：Miran Mavlan、Kevin Ng、Harmanpreet Panesar、Akop Yepremyan、Thomas G. Minehan

  DOI：10.1021/ol500725e

  日期：2014.4.18

  The 3,3'-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3'-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 mu M, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.