(R)-1-[(2S,3S)-3-methoxy-6-oxo-tetrahydro-2H-pyran-2-yl]-2-oxobutyl pivalate | 1449755-46-7

• 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)-1-[(2S,3S)-3-methoxy-6-oxo-tetrahydro-2H-pyran-2-yl]-2-oxobutyl pivalate
• CAS: 1449755-46-7
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: IXUBDXFWGRYSAM-DRZSPHRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-1-[(2S,3S)-3-methoxy-6-oxo-tetrahydro-2H-pyran-2-yl]-2-oxobutyl pivalate 、 1,2-乙二硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以67%的产率得到(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
• 作为产物：
  描述：

  (S)-2-[(2S,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-propiony-l-1,4-dioxan-2-yl]-2-methoxyethyl acetate 在 4-二甲氨基吡啶 、 iron(III) chloride 、 5%-palladium/activated carbon 、 水 、 氢气 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 35.0h， 生成 (R)-1-[(2S,3S)-3-methoxy-6-oxo-tetrahydro-2H-pyran-2-yl]-2-oxobutyl 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