| 1238374-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1238374-28-1
• 化学式: C₂₇H₄₆O₈Si₂
• 分子量: 554.828
• InChiKey: CEKQLMACZRJVAM-KTXQOAOTSA-N

物化性质

• 沸点：
  616.6±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  106.84
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  、 2-(三甲基硅烷基)乙氧甲基氯 在 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以74%的产率得到(1S,4a'R,7'R,8'R,8a'R)-2',2'-di-tert-butyl-8'-((triethylsilyl)oxy)-5,7,7'-tris((2-(trimethylsilyl)ethoxy)methoxy)-4a',7',8',8a'-tetrahydro-3H,4'H-spiro[isobenzofuran-1,6'-pyrano[3,2-d][1,3,2]dioxasiline]
  参考文献：
  名称：

  Total synthesis of (+)-papulacandin D

  摘要：

  A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.093
• 作为产物：
  描述：

  2',2'-bis(1,1-dimethylethyl)-4'a,7',8',8'a-tetrahydro-5,7-bis(phenylmethoxy)-8'-triethylsilyloxy-(1S,4'aR,7'S,8'R,8'aR)-spiro[isobenzofuran-1(3H),6'(4'H)-pyrano[3,2-d][1,3,2]dioxasilin]-7'-ol 在 5% Pd(II)/C(eggshell) 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 1.0 ℃ 、101.33 kPa 条件下， 反应 11.17h， 以88%的产率得到
  参考文献：
  名称：

  Total synthesis of (+)-papulacandin D

  摘要：

  A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.093