1,5-anhydro-2-dimethylsilyl-4,6-(O-isopropylidene)-3-(O-methyl)-2-deoxy-D-arabino-hex-1-enitol | 1238373-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2-dimethylsilyl-4,6-(O-isopropylidene)-3-(O-methyl)-2-deoxy-D-arabino-hex-1-enitol
• CAS: 1238373-62-0
• 化学式: C₁₂H₂₂O₄Si
• 分子量: 258.39
• InChiKey: WNLURUMHWGVARC-FBIMIBRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  二甲基一氯硅烷 、 1,2-dideoxy-4,6-O-isopropylidene-3-O-methyl-D-arabino-hex-1-enopyranose 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.04h， 以44%的产率得到1,5-anhydro-2-dimethylsilyl-4,6-(O-isopropylidene)-3-(O-methyl)-2-deoxy-D-arabino-hex-1-enitol
  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