(3R,4S,5R)-3,4,5-tris(methoxymethoxy)tetrahydro-2H-pyran-2-one | 1057402-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S,5R)-3,4,5-tris(methoxymethoxy)tetrahydro-2H-pyran-2-one
• CAS: 1057402-36-4
• 化学式: C₁₁H₂₀O₈
• 分子量: 280.275
• InChiKey: WSDREVJEBBQCCS-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethyltitanocene 、 (3R,4S,5R)-3,4,5-tris(methoxymethoxy)tetrahydro-2H-pyran-2-one 以 甲苯 为溶剂， 反应 18.0h， 以74%的产率得到(3R,4S,5R)-3,4,5-tris(methoxymethoxy)-2-methylideneoxane
  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
• 作为产物：
  描述：

  2,3,4-tri-O-(methoxymethyl)-D-xylopyranose 在 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(3R,4S,5R)-3,4,5-tris(methoxymethoxy)tetrahydro-2H-pyran-2-one
  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