1α-[2-cyano-2-(ethoxycarbonyl)-1,3-dihydro-2H-inden-5-yl]-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose | 1037597-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1α-[2-cyano-2-(ethoxycarbonyl)-1,3-dihydro-2H-inden-5-yl]-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose
• CAS: 1037597-17-3
• 化学式: C₃₄H₃₃NO₇
• 分子量: 567.639
• InChiKey: OXXUSAUHALTKAF-YESINTGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  111.92
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1α-ethynyl-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose 、 ethyl 2-cyano-2-(prop-2-ynyl)-pent-4-yne-1-oate 在 RhCl(PPh₃)3 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以53%的产率得到1α-[2-cyano-2-(ethoxycarbonyl)-1,3-dihydro-2H-inden-5-yl]-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose
  参考文献：
  名称：

  Co- and homocyclotrimerization reactions of protected 1-alkynyl-2-deoxyribofuranose. Synthesis of C-nucleosides, C-di- and C-trisaccharide analogues

  摘要：

  Cyclotrimerization of beta- or alpha-ethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose with alpha,omega-diynes proceeded smoothly under Rh-catalysis to afford the corresponding beta- or a-benzene C-nucleoside derivatives. Analogous co-cyclotrimerization of alpha- or beta-propynyl- and -phenylethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose with alpha,omega-diynes gave the corresponding arene derivatives only under microwave irradiation in the presence of a Rh-catalyst in moderate yields. Attempted homocyclotrimerization of beta- or alpha-ethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose under Rh-catalysis led only to enynes while the use of Ru-catalyst gave the desired 1,2,4- and 1,3,5-tri-(2-deoxyribofuranose-1-yl)benzene. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.046