((2R,3R,4S,5R,6S)-4-(benzoyloxy)-3,5-dihydroxy-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)methyl benzoate | 1403377-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3R,4S,5R,6S)-4-(benzoyloxy)-3,5-dihydroxy-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)methyl benzoate
• CAS: 1403377-44-5
• 化学式: C₂₇H₂₆O₇S
• 分子量: 494.565
• InChiKey: HRPYOUDQKSPMDC-AHPXAKOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4S,5R,6S)-4-(benzoyloxy)-3,5-dihydroxy-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)methyl benzoate 、 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 以72%的产率得到2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-benzoyl-D-glucopyranoside
  参考文献：
  名称：

  Convergent synthesis and cytotoxic activities of 26-thio- and selenodioscin

  摘要：

  Convergent block syntheses of 26-thio- and selenodioscin have been achieved by developing the highly stereoselective 1,2-trans glycosylations of chacotriosyl imidate without recourse to neighboring group assistance. Both thiodioscin and selenodioscin possess cytotoxic activities similar to dioscin, a natural spirostanol glycoside. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.05.018
• 作为产物：
  描述：

  1-(苯甲酰基氧基)-1H-1,2,3-苯并噻唑 、 1-硫代-b-甲基葡萄糖甙-4-甲基苯酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72.9%的产率得到((2R,3R,4S,5R,6S)-4-(benzoyloxy)-3,5-dihydroxy-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)methyl benzoate
  参考文献：
  名称：

  Discovery of the First Series of Small Molecule H5N1 Entry Inhibitors

  摘要：

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Inhibition of H5N1 entry into cells may be an effective strategy. We report the first three small molecule inhibitors saponins with 3-O-beta-chacotriosyl residue, which Showed potent inhibitory activity with IC50 of 7.22-9.25 mu M. The subsequent SAR studies showed the 3-O-beta-chacotriosyl residue was essential for the activity, and the aglycone structure also affected the activity.

  DOI：

  10.1021/jm900275m