(1S,4a'R,7'R,8'R,8a'R)-2',2'-di-tert-butyl-5,7,7'-trihydroxy-4a',7',8',8a'-tetrahydro-3H,4'H-spiro[isobenzofuran-1,6'-pyrano[3,2-d][1,3,2]dioxasilin]-8'-yl (2E,4E)-hexa-2,4-dienoate | 1238374-72-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,4a'R,7'R,8'R,8a'R)-2',2'-di-tert-butyl-5,7,7'-trihydroxy-4a',7',8',8a'-tetrahydro-3H,4'H-spiro[isobenzofuran-1,6'-pyrano[3,2-d][1,3,2]dioxasilin]-8'-yl (2E,4E)-hexa-2,4-dienoate
• CAS: 1238374-72-5
• 化学式: C₂₇H₃₈O₉Si
• 分子量: 534.679
• InChiKey: JNGGOUVVRXIUFO-BBLTZNSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  37.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  123.91
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  (1S,4a'R,7'R,8'R,8a'R)-2',2'-di-tert-butyl-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]dioxasilin]-8'-yl (2E,4E)-hexa-2,4-dienoate 在 丁硫醇 、 magnesium bromide 、 水 作用下， 以 乙醚 、 硝基甲烷 为溶剂， 以100%的产率得到(1S,4a'R,7'R,8'R,8a'R)-2',2'-di-tert-butyl-5,7,7'-trihydroxy-4a',7',8',8a'-tetrahydro-3H,4'H-spiro[isobenzofuran-1,6'-pyrano[3,2-d][1,3,2]dioxasilin]-8'-yl (2E,4E)-hexa-2,4-dienoate
  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