1,2-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C,3-O-(o-phenylenemethylene)-α-D-ribofuranose | 1242274-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1,2-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C,3-O-(o-phenylenemethylene)-α-D-ribofuranose
• 英文别名: [(3R,3'aR,5'R,6'aR)-2',2'-dimethylspiro[1H-2-benzofuran-3,6'-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole]-5'-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 1242274-26-5
• 化学式: C₂₁H₃₂O₅Si
• 分子量: 392.568
• InChiKey: JPUZCBAWNXUIIW-BMQTXXJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C,3-O-(o-phenylenemethylene)-α-D-ribofuranose 、 乙酸酐 在 溶剂黄146 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到1,2,4-tri-O-acetyl-3-C,3-O-(o-phenylenemethylene) β-D-ribopyranose
  参考文献：
  名称：

  The isochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides

  摘要：

  The synthesis of enantiopure tricyclic systems comprising isochroman or dihydroisobenzofuran units integrated with sugar templates has been documented. The alkyne cylotrimerization reaction has been employed with easily accessible sugar diynes for the key bicyclic ring construction and thus a provision to alter the functional groups on the newly formed aromatic rings. By selecting two representative trimerization products, we have synthesized the tricyclic nucleosides by simple synthetic manipulations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.011
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C-ethynyl-3-O-propargyl-α-D-ribofuranose 、 乙炔 在 Wilkinson's catalyst 作用下， 以 甲苯 为溶剂， 以71%的产率得到1,2-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C,3-O-(o-phenylenemethylene)-α-D-ribofuranose
  参考文献：
  名称：

  The isochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides

  摘要：

  The synthesis of enantiopure tricyclic systems comprising isochroman or dihydroisobenzofuran units integrated with sugar templates has been documented. The alkyne cylotrimerization reaction has been employed with easily accessible sugar diynes for the key bicyclic ring construction and thus a provision to alter the functional groups on the newly formed aromatic rings. By selecting two representative trimerization products, we have synthesized the tricyclic nucleosides by simple synthetic manipulations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.011