24,33-Bis-(t.butyl-dimethylsilyl)-9(S)-dihydro-FK 506-9,10-thiocarbonate | 133941-60-3

• 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)-dihydro-FK 506-9,10-thiocarbonate
• 英文别名: (1S,5S,12S,15S,16S,17S,20R,21E,24S,26S,27R,28S,30R)-17-[tert-butyl(dimethyl)silyl]oxy-15-[(E)-1-[(1R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxycyclohexyl]prop-1-en-2-yl]-26,28-dimethoxy-16,22,24,30-tetramethyl-20-prop-2-enyl-3-sulfanylidene-2,4,14,31-tetraoxa-7-azatetracyclo[25.3.1.01,5.07,12]hentriacont-21-ene-6,13,19-trione
• CAS: 133941-60-3；134002-08-7
• 化学式: C₅₇H₉₇NO₁₂SSi₂
• 分子量: 1076.63
• InChiKey: ACAJIFHWHYHAEA-RQMIIXCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.84
• 重原子数：
  73
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  24,33-Bis-(t.butyl-dimethylsilyl)-9(S)-dihydro-FK 506-9,10-thiocarbonate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以78%的产率得到24,33-Bis-(t.butyl-dimethylsilyl)-Δ⁹-FK 506
  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-(t.butyl-dimethylsilyl)-9(S)-dihydro-FK 506 、 N,N'-硫羰基二咪唑 以 1,2-二氯乙烷 为溶剂， 以91%的产率得到24,33-Bis-(t.butyl-dimethylsilyl)-9(S)-dihydro-FK 506-9,10-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