24,33-Bis-(t.butyl-dimethylsilyl)-9(R)-dihydro-FR 900520 | 133941-32-9

• 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(R)-dihydro-FR 900520
• 英文别名: (1R,2R,9S,12S,13S,14S,17R,18E,21S,23S,24R,25S,27R)-14-[tert-butyl(dimethyl)silyl]oxy-12-[(E)-1-[(1R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,2-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-3,10,16-trione
• CAS: 133941-32-9；134002-05-4；148217-45-2
• 化学式: C₅₅H₉₉NO₁₂Si₂
• 分子量: 1022.56
• InChiKey: ZIWBUVFKDAOLFH-JGGXIDBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.32
• 重原子数：
  70
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  24,33-Bis-(t.butyl-dimethylsilyl)-9(R)-dihydro-FR 900520 、 N,N'-硫羰基二咪唑 以 1,2-二氯乙烷 为溶剂， 以88%的产率得到24,33-Bis-(t.butyl-dimethylsilyl)-9(R)-dihydro-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
• 作为产物：
  描述：

  24,33-bis-OTBDMS-ascomycin 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以82%的产率得到24,33-Bis-(t.butyl-dimethylsilyl)-9(R)-dihydro-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

文献信息

• Synthesis of derivatives of FK 506 and FR 900520: modifications at the binding domain
  作者：Gerhard Emmer、Sabine Weber-Roth

  DOI：10.1016/s0040-4020(01)90178-4

  日期：1992.7

  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.