2,3,4-trimethoxy-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)benzaldehyde | 1585169-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-trimethoxy-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)benzaldehyde
• CAS: 1585169-37-4
• 化学式: C₄₄H₄₆O₉
• 分子量: 718.844
• InChiKey: CUXFXRSWZWBDFU-NMGQROGNSA-N

物化性质

• 沸点：
  799.9±60.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,3,4-trimethoxy-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)benzaldehyde 在 aluminum (III) chloride 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到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
• 作为产物：
  描述：

  1,2,3-Trimethoxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 氯仿 、 环己烷 为溶剂， 反应 2.25h， 生成 2,3,4-trimethoxy-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-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