(E)-ethyl 4-[(2S,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-propionyl-1,4-dioxan-2-yl]-4-methoxybut-2-enoate | 1449755-36-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 4-[(2S,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-propionyl-1,4-dioxan-2-yl]-4-methoxybut-2-enoate
• 英文别名: ethyl (E,4S)-4-[(2S,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-propanoyl-1,4-dioxan-2-yl]-4-methoxybut-2-enoate
• CAS: 1449755-36-5
• 化学式: C₁₈H₃₀O₈
• 分子量: 374.431
• InChiKey: LLGGSPNSDIIIEG-GSDAVCKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-[(2S,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-propionyl-1,4-dioxan-2-yl]-4-methoxybut-2-enoate 在 iron(III) chloride 、 5%-palladium/activated carbon 、 水 、 氢气 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 (5S,6R)-6-((R)-1-hydroxy-2-oxobutyl)-5-methoxytetrahydro-2H-pyran-2-one
  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)-2,3-dimethoxy-2,3-dimethyl-5-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-8-ol 在 5%-palladium/activated carbon 、 氢气 、 sodium hydride 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 30.25h， 生成 (E)-ethyl 4-[(2S,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-propionyl-1,4-dioxan-2-yl]-4-methoxybut-2-enoate
  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.