(2R,3R,4aR,8S,8aS)-2,3,8-trimethoxy-2,3-dimethylhexahydro-2H-pyrano[3,4-b][1,4]dioxin-5-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2R,3R,4aR,8S,8aS)-2,3,8-trimethoxy-2,3-dimethylhexahydro-2H-pyrano[3,4-b][1,4]dioxin-5-ol
• 英文别名: (2R,3R,4aR,8S,8aS)-2,3,8-trimethoxy-2,3-dimethyl-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-ol
• 化学式: C₁₂H₂₂O₇
• 分子量: 278.302
• InChiKey: SVGBCXSHCLOODU-PMEYNAPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4aR,8S,8aS)-2,3,8-trimethoxy-2,3-dimethylhexahydro-2H-pyrano[3,4-b][1,4]dioxin-5-ol 在 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 (S)-ethyl 4-((2S,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-propionyl-1,4-dioxan-2-yl)-4-methoxybutanoate
  参考文献：
  名称：

  A carbohydrate based chiron approach to the lactone intermediate employed in the synthesis of BC-ring fragment of (+)-spirastrellolide A

  摘要：

  A concise and stereoselective synthesis of the key intermediate used for constructing the BC-ring fragment of (+)-spirastrellolide A is described. The synthetic sequence represents a chiron approach that employs readily available and inexpensive L-arabinose and sets up the stereochemical triad at C20-C22 all from the sugar. This lactone can be used to assemble the spiroketal in the Southern Half through a cyclic acetal-tethered ring-closing metathesis strategy, and is poised for connecting with the Northern Half at C24-C25. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.07.009
• 作为产物：
  描述：

  (2R,3R,4aR,8S,8aS)-5-(benzyloxy)-2,3,8-trimethoxy-2,3-dimethylhexahydro-2H-pyrano[3,4-b][1,4]dioxine 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以95%的产率得到(2R,3R,4aR,8S,8aS)-2,3,8-trimethoxy-2,3-dimethylhexahydro-2H-pyrano[3,4-b][1,4]dioxin-5-ol
  参考文献：
  名称：

  A carbohydrate based chiron approach to the lactone intermediate employed in the synthesis of BC-ring fragment of (+)-spirastrellolide A

  摘要：

  A concise and stereoselective synthesis of the key intermediate used for constructing the BC-ring fragment of (+)-spirastrellolide A is described. The synthetic sequence represents a chiron approach that employs readily available and inexpensive L-arabinose and sets up the stereochemical triad at C20-C22 all from the sugar. This lactone can be used to assemble the spiroketal in the Southern Half through a cyclic acetal-tethered ring-closing metathesis strategy, and is poised for connecting with the Northern Half at C24-C25. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.07.009

文献信息

• A carbohydrate based chiron approach to the lactone intermediate employed in the synthesis of BC-ring fragment of (+)-spirastrellolide A
  作者：Chao-Chao Wang、Yu Tang、Ka Yang、Xiao-Yu Li、Yi-Biao Wu、Richard P. Hsung

  DOI：10.1016/j.tet.2013.07.009

  日期：2013.9

  A concise and stereoselective synthesis of the key intermediate used for constructing the BC-ring fragment of (+)-spirastrellolide A is described. The synthetic sequence represents a chiron approach that employs readily available and inexpensive L-arabinose and sets up the stereochemical triad at C20-C22 all from the sugar. This lactone can be used to assemble the spiroketal in the Southern Half through a cyclic acetal-tethered ring-closing metathesis strategy, and is poised for connecting with the Northern Half at C24-C25. Published by Elsevier Ltd.