3-O-Methyl-3-C-ethinyl-1,2:5,6-di-O-isopropyliden-α-D-allofuranose | 56998-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-Methyl-3-C-ethinyl-1,2:5,6-di-O-isopropyliden-α-D-allofuranose
• 英文别名: (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole；(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-ethynyl-6-methoxy-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole
• CAS: 56998-55-1
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: LPWKRQJJTWWJNR-BJIWRROBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-Methyl-3-C-ethinyl-1,2:5,6-di-O-isopropyliden-α-D-allofuranose 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， -10.0~20.0 ℃ 、101.33 kPa 条件下， 反应 55.0h， 生成 (3aR,4aR,5R,8aR,8bR)-8a-ethoxy-2,2-dimethyl-8-methylene-3a,4a,5,8,8a,8b-hexahydrobenzofuro[2,3-d][1,3]dioxol-5-ol
  参考文献：
  名称：

  A Tandem Enyne/Ring Closing Metathesis Approach to 4-Methylene-2-cyclohexenols: An Efficient Entry to Otteliones and Loloanolides

  摘要：

  A short and efficient approach to a 4-methylene-2-cyclohexenone substructure present in ottellones and loloanolides Is described. This strategy involves a tandem enyne/ring closing metathesis as the key reaction to construct this labile core unit

  DOI：

  10.1021/ol2029838
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 3-O-Methyl-3-C-ethinyl-1,2:5,6-di-O-isopropyliden-α-D-allofuranose
  参考文献：
  名称：

  A Tandem Enyne/Ring Closing Metathesis Approach to 4-Methylene-2-cyclohexenols: An Efficient Entry to Otteliones and Loloanolides

  摘要：

  A short and efficient approach to a 4-methylene-2-cyclohexenone substructure present in ottellones and loloanolides Is described. This strategy involves a tandem enyne/ring closing metathesis as the key reaction to construct this labile core unit

  DOI：

  10.1021/ol2029838

文献信息

• An Efficient Copper-Catalyzed Three-Component Synthesis of 3-C-Linked Glycosyl Iminocoumarins
  作者：Krishna Kaliappan、Kalanidhi Palanichamy、Sankar Suravarapu

  DOI：10.1055/s-0031-1289763

  日期：2012.6

  An efficient general strategy was developed for the synthesis of previously unknown 3-C-linked glycosyl iminocoumarins. The strategy involves a copper-catalyzed multicomponent reaction of sugar-derived alkynes with tosyl azide and salicylaldehyde to give a diverse array of glycosyl iminocoumarins in good yields. These compounds can serve as appropriate precursors for the synthesis of the corresponding coumarin 3-C-glycosides.