(2S,3S,4S,5R)-2-(2-methoxybenzyl)-3,4,5-tris(methoxymethoxy)tetrahydro-2H-pyran | 1057402-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3S,4S,5R)-2-(2-methoxybenzyl)-3,4,5-tris(methoxymethoxy)tetrahydro-2H-pyran
• CAS: 1057402-38-6
• 化学式: C₁₉H₃₀O₈
• 分子量: 386.442
• InChiKey: HOUIEYMJESMTME-RDGPPVDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (3R,4S,5R)-3,4,5-tris(methoxymethoxy)-2-methylideneoxane 、 三氟甲磺酸2-甲氧基苯基酯 在 9-硼双环[3.3.1]壬烷 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以74%的产率得到(2S,3S,4S,5R)-2-(2-methoxybenzyl)-3,4,5-tris(methoxymethoxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Synthesis and an Evaluation of the Bioactivity of the C-Glycoside of Pseudopterosin A Methyl Ether

  摘要：

  The Suzuki-Miyaura cross-coupling protocol was applied to the synthesis of 1a, the C-glycoside analogue of PsA methyl ether. This marks the first construction of a C-glycoside for this class of marine natural products, thereby offering an opportunity to compare its bioactivity to the natural substances. Its activity profile resembled that of PsA (1) and PsA O-methyl ether (1b) when assayed for its anti-inflammatory activity and its ability to inhibit phagocytosis. We conclude that the intact structure is present when a pseudopterosin expresses its anti-inflammatory and phagocytosis inhibitory properties and that they are, therefore, not likely to be prodrugs. Results show that 1a is an effective binding agent toward the A(2A) and A(3) adenosine receptors, displaying IC50 values of 20 and 10 mu M, respectively.

  DOI：

  10.1021/jo801432t