(R)-(2-ethyl-1,3-dithiolan-2-yl)[(2S,3S)-3-methoxy-6-oxotetra-hydro-2H-pyran-2-yl]methyl pivalate | 1449755-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (R)-(2-ethyl-1,3-dithiolan-2-yl)[(2S,3S)-3-methoxy-6-oxotetra-hydro-2H-pyran-2-yl]methyl pivalate
• 英文别名: [(R)-(2-ethyl-1,3-dithiolan-2-yl)-[(2S,3S)-3-methoxy-6-oxooxan-2-yl]methyl] 2,2-dimethylpropanoate
• CAS: 1449755-47-8
• 化学式: C₁₇H₂₈O₅S₂
• 分子量: 376.538
• InChiKey: LTZJFFXFYITPBK-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  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 4-二甲氨基吡啶 、 iron(III) chloride 、 5%-palladium/activated carbon 、 三氟化硼乙醚 、 水 、 氢气 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 63.0h， 生成 (R)-(2-ethyl-1,3-dithiolan-2-yl)[(2S,3S)-3-methoxy-6-oxotetra-hydro-2H-pyran-2-yl]methyl pivalate
  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.