3,5-bis(benzyloxy)-2-iodo-1-(tetrahydropyran-2-yloxymethyl)benzene | 1238373-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(benzyloxy)-2-iodo-1-(tetrahydropyran-2-yloxymethyl)benzene
• CAS: 1238373-99-3
• 化学式: C₂₆H₂₇IO₄
• 分子量: 530.402
• InChiKey: GOIVDKDZZPPCRU-UHFFFAOYSA-N

物化性质

• 沸点：
  611.4±55.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-4,6-O-[bis(1,1-dimethylethyl)silylene]-2-deoxy-1-C-(hydroxydimethylsilyl)-3-O-(triethylsilyl)-D-arabino-1-hexenitol 、 3,5-bis(benzyloxy)-2-iodo-1-(tetrahydropyran-2-yloxymethyl)benzene 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到1,5-anhydro-4,6-O-[bis(1,1-dimethylethyl)silylene]-1-C-[2',4'-bis(phenylmethoxy)-6'-[(tetrahydropyran-2''-yl)methoxy]phenyl]-2-deoxy-3-O-triethylsilyl-D-arabino-1-hexenitol
  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-iodo-3,5-bis(phenylmethoxy)benzenemethanol 、 3,4-二氢-2H-吡喃 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到3,5-bis(benzyloxy)-2-iodo-1-(tetrahydropyran-2-yloxymethyl)benzene
  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