(2S,3S,4aR,6R,8R,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-2,3-dimethoxy-2,3-dimethyl-4a,5,6,7,8,8a-hexahydrobenzo[b][1,4]dioxin-6-ol | 596834-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4aR,6R,8R,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-2,3-dimethoxy-2,3-dimethyl-4a,5,6,7,8,8a-hexahydrobenzo[b][1,4]dioxin-6-ol
• CAS: 596834-62-7
• 化学式: C₁₈H₃₆O₆Si
• 分子量: 376.566
• InChiKey: XBGVDYAJGVEMBX-FLMUCADWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4aR,6R,8R,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-2,3-dimethoxy-2,3-dimethyl-4a,5,6,7,8,8a-hexahydrobenzo[b][1,4]dioxin-6-ol 在 伯吉斯试剂 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 (2'S,3'S,3R,4R,5S)-3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohex-1-ene-3,4,5-triol 、
  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：

  (2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate 在 甲醇 、 sodium tetrahydroborate 、 sodium periodate 、 phosphate buffer 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 80.0h， 生成 (2S,3S,4aR,6R,8R,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-2,3-dimethoxy-2,3-dimethyl-4a,5,6,7,8,8a-hexahydrobenzo[b][1,4]dioxin-6-ol
  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