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 | 183252-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 183252-93-9
• 化学式: C₁₆H₂₆O₈
• 分子量: 346.378
• InChiKey: HHASXAQSNUWICC-HKGQCULVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  右旋奎宁酸 在 Amberlite(R) IR 120(H) 、 camphor-10-sulfonic acid 、 原甲酸三甲酯 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 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
  参考文献：
  名称：

  Approaches to the synthesis of 3-fluoroshikimic acids

  摘要：

  Exploitation of the dual dehydrating and fluorodeoxygenating properties of the dialkylaminosulfurtrifluorides has allowed access to the C3-fluorinated analogues of (-)-shikimic acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.092

文献信息

• Dehydration of Quinate Derivatives: Synthesis of a Difluoromethylene Homologue of Shikimic Acid
  作者：Julian M. Box、Laurence M. Harwood、Jane L. Humphreys、Gareth A. Morris、Perrine M. Redon、Roger C. Whitehead

  DOI：10.1055/s-2002-19772

  日期：——

  An optimised procedure for the conversion of a quinate to shikimate structure has been developed using Martin"s Sulfurane Ph2S[OC(CF3)2Ph]2}. This protocol has been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid.

  我们利用马丁硫醚 Ph2S[OC(CF3)2Ph]2} 开发出了一种将醌酯结构转化为莽草酸结构的优化程序。在合成莽草酸的新型二氟亚甲基同系物时利用了这一程序。
• A Practical Synthesis of Enantiopure (R)-4-Hydroxy-2-cyclohexen-1-one
  作者：Olaf Gebauer、Reinhard Brückner

  DOI：10.1002/jlac.199619961010

  日期：1996.10

  The title compound R-4a was prepared from (–)-quinic acid (1) in 6 steps in 18% overall yield (Scheme 3) and with 100% enantiomeric purity (Figure 1). The initiating step is the regio- and stereoselective acetalization of the trans-oriented vicinal OH groups of 1 (+ 5 8). Alcohol R-4a can be protected as the 2-ethoxyethyl ether R-4e (78%).

  标题化合物R - 4a由（-）-奎尼酸（1）分6步制备，总收率为18％（方案3），对映体纯度为100％（图1）。起始步骤是反式邻位OH基团为1（+ 5 8）的区域和立体选择性缩醛化。可以将醇R - 4a保护为2-乙氧基乙基醚R - 4e（78％）。
• First Efficient Syntheses of 1-, 4-, and 5-Caffeoylquinic Acid
  作者：Michael Sefkow、Alexandra Kelling、Uwe Schilde

  DOI：10.1002/1099-0690(200107)2001:14<2735::aid-ejoc2735>3.0.co;2-i

  日期：2001.7