(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(5-methyl-furan-2-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol | 890707-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(5-methyl-furan-2-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 890707-40-1
• 化学式: C₁₇H₂₄O₇
• 分子量: 340.373
• InChiKey: AQBDNNLYFFBORD-LHNVCGPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  79.52
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(5-methyl-furan-2-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 gold(III) chloride 、 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.17h， 生成 (1R,3'aR,5'R,6'aR)-5'-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2',2',5-trimethylspiro[3H-2-benzofuran-1,6'-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole]-4-ol
  参考文献：
  名称：

  Synthesis of spiroannulated dihydroisobenzofuranylated monosaccharides

  摘要：

  An efficient synthesis of spiroannulated dihydroisobenzofurans is achieved using easily accessible carbohydrate-derived furanyl propargyl ethers via an AuCl3 promoted intramolecular Diels-Alder (IMDA) reaction. The scope of the spiroannulation protocol was demonstrated using a diverse range of pentofuranosyl, hexofuransoyl and hexopyranosyl derived substrates in order to synthesize spiroannulated dihydroisobenzofurans. The reaction is high yielding, moisture tolerant, fast and uses only a catalytic amount of AuCl3. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.016
• 作为产物：
  描述：

  2-甲基呋喃 、 1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(5-methyl-furan-2-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  Synthesis of spiroannulated dihydroisobenzofuranylated monosaccharides

  摘要：

  An efficient synthesis of spiroannulated dihydroisobenzofurans is achieved using easily accessible carbohydrate-derived furanyl propargyl ethers via an AuCl3 promoted intramolecular Diels-Alder (IMDA) reaction. The scope of the spiroannulation protocol was demonstrated using a diverse range of pentofuranosyl, hexofuransoyl and hexopyranosyl derived substrates in order to synthesize spiroannulated dihydroisobenzofurans. The reaction is high yielding, moisture tolerant, fast and uses only a catalytic amount of AuCl3. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.016