(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(5-methyl-furan-2-yl)-6-prop-2-ynyloxy-tetrahydro-furo[2,3-d][1,3]dioxole | 890707-43-4

• 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)-6-prop-2-ynyloxy-tetrahydro-furo[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-(5-methylfuran-2-yl)-6-prop-2-ynoxy-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole
• CAS: 890707-43-4
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: DENDVNAHEBMNOE-UJRRQQMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  68.5
• 氢给体数：
  0
• 氢受体数：
  7

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)-6-prop-2-ynyloxy-tetrahydro-furo[2,3-d][1,3]dioxole 在 gold(III) chloride 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以93%的产率得到(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 在 正丁基锂 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(5-methyl-furan-2-yl)-6-prop-2-ynyloxy-tetrahydro-furo[2,3-d][1,3]dioxole
  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