| 1238373-97-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• CAS: 1238373-97-1
• 化学式: C₁₆H₃₂O₄Si₂
• 分子量: 344.599
• InChiKey: OIILQAPSXUAHAW-BZPMIXESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,5-anhydro-4,6-O-[bis(1,1-dimethylethyl)silylene]-2-deoxy-1-C-(dimethyl(silyl))-3-O-(triethylsilyl)-D-arabino-1-hexenitol 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 水 、 氧气 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以52%的产率得到1,5-anhydro-4,6-O-[bis(1,1-dimethylethyl)silylene]-2-deoxy-1-C-(hydroxydimethylsilyl)-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