R-methyl 5-((2S,5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-yl)hex-3-ynoate | 1248342-89-3

• 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: R-methyl 5-((2S,5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-yl)hex-3-ynoate
• CAS: 1248342-89-3
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: GPESCAJESZANSL-IPOQPSJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  R-methyl 5-((2S,5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-yl)hex-3-ynoate 在 10% palladium on carbon 、 氢气 作用下， 生成 R-methyl 5-((2S,5S,6R)-5-acetoxy-6-(acetoxymethyl)-tetrahydro-2H-pyran-2-yl)hexanoate
  参考文献：
  名称：

  Stereoselective C-Glycosidations with Achiral and Enantioenriched Allenylsilanes

  摘要：

  Allenylsilanes are used as carbon nucleophiles in highly stereoselective Lewis acid-promoted C-glycosidations, resulting in the introduction of an internal alkyne with an adjacent stereocenter. Both achiral and chiral allenylsilanes form the desired products with high diastereoselectivity, where the nucleophile adds exclusively to the alpha-face of the intermediate oxonium ion. Reactions with glucal and galactal afford dihydropyran products, while reactions with a ribose derivative yield dihydrofuran products.

  DOI：

  10.1021/ol1019629
• 作为产物：
  描述：

  S-methyl 3-(dimethyl(phenyl)silyl)hexa-3,4-dienoate 、 乙酰化葡萄烯糖 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以64%的产率得到R-methyl 5-((2S,5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-yl)hex-3-ynoate
  参考文献：
  名称：

  Stereoselective C-Glycosidations with Achiral and Enantioenriched Allenylsilanes

  摘要：

  Allenylsilanes are used as carbon nucleophiles in highly stereoselective Lewis acid-promoted C-glycosidations, resulting in the introduction of an internal alkyne with an adjacent stereocenter. Both achiral and chiral allenylsilanes form the desired products with high diastereoselectivity, where the nucleophile adds exclusively to the alpha-face of the intermediate oxonium ion. Reactions with glucal and galactal afford dihydropyran products, while reactions with a ribose derivative yield dihydrofuran products.

  DOI：

  10.1021/ol1019629