3-(2-(4-methoxybenzoyl)-thiophenyl)-3,4,5-tri-O-acetyl-β-D-glucuronic acid methyl ester | 1215169-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-(4-methoxybenzoyl)-thiophenyl)-3,4,5-tri-O-acetyl-β-D-glucuronic acid methyl ester
• CAS: 1215169-55-3
• 化学式: C₂₅H₂₆O₁₂S
• 分子量: 550.54
• InChiKey: VXEZZTAJHVMERU-KFKQDCOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3-(2-(4-methoxybenzoyl)-thiophenyl)-3,4,5-tri-O-acetyl-β-D-glucuronic acid methyl ester 在 sodium cyanoborohydride 、 三甲基氯硅烷 、 水 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 0.58h， 以92%的产率得到3-(2-(4-methoxybenzyl)-thiophenyl)-β-D-glucuronic methyl ester
  参考文献：
  名称：

  Synthesis of isotopically labelled SGLT inhibitors and their metabolites

  摘要：

  Isotopically labelled analogues of two structurally very similar SGLT inhibitors AVE2268 (1a) and AVE8887 (1b) have been synthesized by various routes. The radioactive labelled [C-14]-AVE2268 was prepared in five steps including a Friedel-Crafts acylation as the key step for the C-14-label introduction. For [C-14]-AVE8887 the same synthetic approach was not successful and therefore an alternative thiophene metallation/Weinreb amide sequence was developed. This pathway was also applied to obtain stable isotopically labelled analogues of both AVE2268 and AVE8887. Finally, the synthesis of two metabolites, sulfate 12 and glucuronide 13 were achieved by applying interesting protecting group and oxidation strategies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.12.003
• 作为产物：
  描述：

  (3-hydroxythiophen-2-yl)-(4-methoxyphenyl)-methanone 、 乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 四丁基溴化铵 、 potassium carbonate 、 silver carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以65%的产率得到3-(2-(4-methoxybenzoyl)-thiophenyl)-3,4,5-tri-O-acetyl-β-D-glucuronic acid methyl ester
  参考文献：
  名称：

  Synthesis of isotopically labelled SGLT inhibitors and their metabolites

  摘要：

  Isotopically labelled analogues of two structurally very similar SGLT inhibitors AVE2268 (1a) and AVE8887 (1b) have been synthesized by various routes. The radioactive labelled [C-14]-AVE2268 was prepared in five steps including a Friedel-Crafts acylation as the key step for the C-14-label introduction. For [C-14]-AVE8887 the same synthetic approach was not successful and therefore an alternative thiophene metallation/Weinreb amide sequence was developed. This pathway was also applied to obtain stable isotopically labelled analogues of both AVE2268 and AVE8887. Finally, the synthesis of two metabolites, sulfate 12 and glucuronide 13 were achieved by applying interesting protecting group and oxidation strategies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.12.003