(5S)-3-(4-methoxybenzyl)-5-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)dihydrofuran-2(3H)-one | 1242653-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S)-3-(4-methoxybenzyl)-5-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)dihydrofuran-2(3H)-one
• CAS: 1242653-86-6
• 化学式: C₄₆H₄₈O₈
• 分子量: 728.882
• InChiKey: KSYLPWXWVKNBJV-OIYMLQFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  54.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  甲醇 、 (5S)-3-(4-methoxybenzyl)-5-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)dihydrofuran-2(3H)-one 在 对甲苯磺酸 作用下， 生成 methyl (4S)-4-hydroxy-2-(4-methoxybenzyl)-4-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)butanoate
  参考文献：
  名称：

  Synthesis of pyridazine and thiazole analogs as SGLT2 inhibitors

  摘要：

  With anticipation of the improvement in biological aspects in our SGLT2 program, novel pyridazinyl and thiazolyl analogs were designed and efficiently synthesized. The installation of the pyridazine ring at the anomeric carbon of D-glucopyranose was carried out in a stereoselective fashion. On the other hand, a series of thiazolyl analogs was also synthesized through a coupling reaction between perbenzyl gluconolactone 9 and 2-lithiothiazole. Biological activities of the compounds thus prepared were evaluated by the in vitro SGLT2 inhibition assay. Considering assay results, the novel benzylpyridazinyl and benzyl-thiazolyl analogs, disclosed in this article, could be a quick reference to prospective SGLT2 inhibitors useful for pharmacotherapy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.076
• 作为产物：
  描述：

  ethyl (5S)-3-(4-methoxybenzyl)-2-oxo-5-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)tetrahydrofuran-3-carboxylate 在 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以960 mg的产率得到(5S)-3-(4-methoxybenzyl)-5-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis of pyridazine and thiazole analogs as SGLT2 inhibitors

  摘要：

  With anticipation of the improvement in biological aspects in our SGLT2 program, novel pyridazinyl and thiazolyl analogs were designed and efficiently synthesized. The installation of the pyridazine ring at the anomeric carbon of D-glucopyranose was carried out in a stereoselective fashion. On the other hand, a series of thiazolyl analogs was also synthesized through a coupling reaction between perbenzyl gluconolactone 9 and 2-lithiothiazole. Biological activities of the compounds thus prepared were evaluated by the in vitro SGLT2 inhibition assay. Considering assay results, the novel benzylpyridazinyl and benzyl-thiazolyl analogs, disclosed in this article, could be a quick reference to prospective SGLT2 inhibitors useful for pharmacotherapy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.076