(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(4-(methoxy-d3)benzoyl)thiophen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1215169-74-6

• 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)-2-(acetoxymethyl)-6-((2-(4-(methoxy-d3)benzoyl)thiophen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1215169-74-6
• 化学式: C₂₆H₂₈O₁₂S
• 分子量: 567.543
• InChiKey: NHELDRUPAZJFBS-NHDXIIDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(4-(methoxy-d3)benzoyl)thiophen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 三甲基氯硅烷 、 氰基硼氘化钠 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 3-(2-(4-[CD3]-methoxy-[CD2]-benzyl)thiophenyl)-β-D-glucopyranoside
  参考文献：
  名称：

  10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds-synthesis of compounds labelled with long-lived isotopes Session 17, Thursday, June 18, 2009

  摘要：

  本节是第一节的延续。本节介绍了一些详细描述氚化物合成的方法，以及关于多居里级氚处理方法的讨论。此外，还详细描述了多种同位素标记化合物的制备方法。版权所有 © 2010 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1773
• 作为产物：
  描述：

  4-[CD3]-methoxy-N-methoxy-N-methyl-benzamide 在 potassium carbonate 、 boron tribromide-methyl sulfide complex 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 16.5h， 生成 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(4-(methoxy-d3)benzoyl)thiophen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds-synthesis of compounds labelled with long-lived isotopes Session 17, Thursday, June 18, 2009

  摘要：

  本节是第一节的延续。本节介绍了一些详细描述氚化物合成的方法，以及关于多居里级氚处理方法的讨论。此外，还详细描述了多种同位素标记化合物的制备方法。版权所有 © 2010 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1773

文献信息

• Synthesis of isotopically labelled SGLT inhibitors and their metabolites
  作者：Volker Derdau、Thorsten Fey、Jens Atzrodt

  DOI：10.1016/j.tet.2009.12.003

  日期：2010.2

  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.