(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 845440-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 845440-59-7
• 化学式: C₅₄H₇₇NO₁₃SSi₂
• 分子量: 1036.44
• InChiKey: NODGGYYFIHLPLX-SQLDMSABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.36
• 重原子数：
  71.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  154.59
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 四丁基氟化铵 、 溶剂黄146 作用下， 以80%的产率得到(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-7-hydroxy-10-{(S)-hydroxy-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-methyl}-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Estrogen Receptor Ligands. 12. Synthesis of the Major Metabolites of an ERα-Selective, Dihydrobenzoxathiin Antagonist for Osteoporosis

  摘要：

  During the course of drug metabolism studies, a major metabolite of compound 1 was detected in rhesus monkeys and assigned structure 4. The intriguing biotransformation of 1 leading to 4 was confirmed by a 19-step total synthesis starting from resorcinol (11). the key feature of which was the construction of the oxygen bridge utilizing a phenolic oxidation and trapping sequence. In addition.. the synthesis of a related metabolite (5) is described.

  DOI：

  10.1021/ol047741f
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate 、 (6R)-6-[(S)-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-triethylsilyloxymethyl]-3-tri(propan-2-yl)silyloxy-6H-benzo[c]thiochromen-8-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Estrogen Receptor Ligands. 12. Synthesis of the Major Metabolites of an ERα-Selective, Dihydrobenzoxathiin Antagonist for Osteoporosis

  摘要：

  During the course of drug metabolism studies, a major metabolite of compound 1 was detected in rhesus monkeys and assigned structure 4. The intriguing biotransformation of 1 leading to 4 was confirmed by a 19-step total synthesis starting from resorcinol (11). the key feature of which was the construction of the oxygen bridge utilizing a phenolic oxidation and trapping sequence. In addition.. the synthesis of a related metabolite (5) is described.

  DOI：

  10.1021/ol047741f