methyl (4R,4aS,5aS,9aS,10aR)-4-[tert-butyl(dimethyl)silyl]oxy-5a,9a-dimethoxy-1,4,4a,6,7,8,9,10a-octahydrodibenzo-p-dioxin-2-carboxylate | 596834-67-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (4R,4aS,5aS,9aS,10aR)-4-[tert-butyl(dimethyl)silyl]oxy-5a,9a-dimethoxy-1,4,4a,6,7,8,9,10a-octahydrodibenzo-p-dioxin-2-carboxylate
• CAS: 596834-67-2
• 化学式: C₂₂H₃₈O₇Si
• 分子量: 442.625
• InChiKey: JUTRJKYIIYREJF-XMHKDOOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (4R,4aS,5aS,9aS,10aR)-4-[tert-butyl(dimethyl)silyl]oxy-5a,9a-dimethoxy-1,4,4a,6,7,8,9,10a-octahydrodibenzo-p-dioxin-2-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 methyl (4R,4aR,5aS,9aS,10aR)-4-hydroxy-5a,9a-dimethoxy-1,4,4a,6,7,8,9,10a-octahydrodibenzo-p-dioxin-2-carboxylate
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5
• 作为产物：
  描述：

  methyl (2S,4R,4aR,5aS,9aS,10aR)-2,4-dihydroxy-5a,9a-dimethoxy-3,4,4a,6,7,8,9,10a-octahydro-1H-dibenzo-p-dioxin-2-carboxylate 在 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (4R,4aS,5aS,9aS,10aR)-4-[tert-butyl(dimethyl)silyl]oxy-5a,9a-dimethoxy-1,4,4a,6,7,8,9,10a-octahydrodibenzo-p-dioxin-2-carboxylate
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5