24,33-Bis-(t.butyl-dimethylsilyl)-9(S)-deutero-hydro-FR 900520-9,10-thiocarbonate | 144895-62-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: 24,33-Bis-(t.butyl-dimethylsilyl)-9(S)-deutero-hydro-FR 900520-9,10-thiocarbonate
• CAS: 144895-62-5
• 化学式: C₅₆H₉₇NO₁₂SSi₂
• 分子量: 1065.61
• InChiKey: YSMIQCOISVWJDE-SNXNEKCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.67
• 重原子数：
  72.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  137.52
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  24,33-Bis-(t.butyl-dimethylsilyl)-9(S)-deutero-hydro-FR 900520-9,10-thiocarbonate 在 三乙基硼 、 三正丁基氢锡 作用下， 以 正己烷 、 苯 为溶剂， 反应 18.0h， 以38%的产率得到24,33-Bis-(t.butyl-dimethylsilyl)-9-deutero-Δ⁹-FR 900520
  参考文献：
  名称：

  Synthesis of derivatives of FK 506 and FR 900520: modifications at the binding domain

  摘要：

  The synthesis of 9-deoxo-FK 506 (13a), 9-deoxo-FR 900520 (13b), 9-deoxo-10(R)-deoxy-FR 900520 (14) and its 10(S) isomer 15 is described. Radical deoxygenation/elemination of the 9-di-hydro-9,10-thiocarbonates 5a,5b,6a and 6b gave the 9,10 unsaturated compounds 7a (7b) or 8a (8b) which were further transferred by hydration or hydrogenation. Different E/Z ratios of 7a (7b) were obtainted when nBu3SnH or [(CH3)3Si]3SiH in combination with AIBN or Et3B were used, allowing the selective preparation of both isomers. Two possible reaction mechanisms are discussed.

  DOI：

  10.1016/s0040-4020(01)90178-4
• 作为产物：
  描述：

  24,33-bis-OTBDMS-ascomycin 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 24,33-Bis-(t.butyl-dimethylsilyl)-9(S)-deutero-hydro-FR 900520-9,10-thiocarbonate
  参考文献：
  名称：

  Synthesis of derivatives of FK 506 and FR 900520: modifications at the binding domain

  摘要：

  The synthesis of 9-deoxo-FK 506 (13a), 9-deoxo-FR 900520 (13b), 9-deoxo-10(R)-deoxy-FR 900520 (14) and its 10(S) isomer 15 is described. Radical deoxygenation/elemination of the 9-di-hydro-9,10-thiocarbonates 5a,5b,6a and 6b gave the 9,10 unsaturated compounds 7a (7b) or 8a (8b) which were further transferred by hydration or hydrogenation. Different E/Z ratios of 7a (7b) were obtainted when nBu3SnH or [(CH3)3Si]3SiH in combination with AIBN or Et3B were used, allowing the selective preparation of both isomers. Two possible reaction mechanisms are discussed.

  DOI：

  10.1016/s0040-4020(01)90178-4