(9R,10R,11R,12S,13S)-10,11,12-tris(benzyloxy)-16-chloro-15-(4-ethoxybenzyl)-3,4,5,6,8,9,10,11,12,13-decahydro-2H-9,13-epoxybenzo[h][1,7]dioxacyclopentadecine | 1338728-24-7

• 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: (9R,10R,11R,12S,13S)-10,11,12-tris(benzyloxy)-16-chloro-15-(4-ethoxybenzyl)-3,4,5,6,8,9,10,11,12,13-decahydro-2H-9,13-epoxybenzo[h][1,7]dioxacyclopentadecine
• 英文别名: (1S,16R,17R,18R,19S)-5-chloro-4-[(4-ethoxyphenyl)methyl]-17,18,19-tris(phenylmethoxy)-8,14,20-trioxatricyclo[14.3.1.02,7]icosa-2(7),3,5-triene
• CAS: 1338728-24-7
• 化学式: C₄₇H₅₁ClO₇
• 分子量: 763.371
• InChiKey: JKRYYXJLQDAMGR-VBLURBSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  55.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (9R,10R,11R,12S,13S)-10,11,12-tris(benzyloxy)-16-chloro-15-(4-ethoxybenzyl)-3,4,5,6,8,9,10,11,12,13-decahydro-2H-9,13-epoxybenzo[h][1,7]dioxacyclopentadecine 在 三氯化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以20%的产率得到(9R,10S,11R,12R,13S)-16-chloro-15-(4-ethoxybenzyl)-3,4,5,6,8,9,10,11,12,13-decahydro-2H-9,13-epoxybenzo[h][1,7]dioxacyclopentadecine-10,11,12-triol
  参考文献：
  名称：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents

  摘要：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles possessing methylthiophenyl at the distal ring 40 or ethoxyphenyl at the distal ring 23 showed the best in vitro inhibitory activity in this series to date (40, IC50 = 0.778 nM and 23, IC50 = 0.899 nM) against hSGLT2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.045
• 作为产物：
  描述：

  (3R,4S,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 在 吡啶 、 咪唑 、 三乙基硅烷 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 18-冠醚-6 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 mineral oil 、 苯 为溶剂， 反应 47.58h， 生成 (9R,10R,11R,12S,13S)-10,11,12-tris(benzyloxy)-16-chloro-15-(4-ethoxybenzyl)-3,4,5,6,8,9,10,11,12,13-decahydro-2H-9,13-epoxybenzo[h][1,7]dioxacyclopentadecine
  参考文献：
  名称：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents

  摘要：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles possessing methylthiophenyl at the distal ring 40 or ethoxyphenyl at the distal ring 23 showed the best in vitro inhibitory activity in this series to date (40, IC50 = 0.778 nM and 23, IC50 = 0.899 nM) against hSGLT2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.045