(2S,3R,4R,5S,6S)-3,4,5-tris(benzoyloxy)-6-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-tetrahydro-2H-pyran-2-carboxylic acid | 1174331-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3R,4R,5S,6S)-3,4,5-tris(benzoyloxy)-6-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-tetrahydro-2H-pyran-2-carboxylic acid
• 英文别名: (2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-(1,4-dioxonaphthalen-2-yl)oxane-2-carboxylic acid
• CAS: 1174331-29-3
• 化学式: C₃₇H₂₆O₁₁
• 分子量: 646.607
• InChiKey: HXMSKYJOPFUNBT-AQZMQOMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  [(2R,3S,4R,5S,6S)-4,5-dibenzoyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(1,4-dimethoxynaphthalen-2-yl)oxan-3-yl] benzoate 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以42%的产率得到(2S,3R,4R,5S,6S)-3,4,5-tris(benzoyloxy)-6-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-tetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  β-C-Glycosiduronic acids and β-C-glycosyl compounds: New PTP1B inhibitors

  摘要：

  beta-C-Glycosiduronic acid quinones and beta-C-glycosyl compounds have been synthesized as sugar-based PTP1B inhibitors. Benzoyl protected quinone derivatives (14 and 35) as well as aryl beta-C-glycosyl compounds (18, 22, 23 and 34) showed IC50 values of 0.77-5.27 mu M against PTP1B, with compounds 18 and 23 bearing an acidic function being the most potent. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.091