1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione | 1353743-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione
• CAS: 1353743-39-1
• 化学式: C₂₅H₄₀N₂O₆SSi₂
• 分子量: 552.839
• InChiKey: BSDQDHKKCFMGDJ-YZUZCNPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  91.78
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-噻吩硼酸 、 6-iodo-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine 在 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以33%的产率得到1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 6-aryl-2′-deoxyuridine nucleosides via a Liebeskind cross-coupling methodology

  摘要：

  Hitherto, the synthesis of 6-substituted 2'-deoxyuridine nucleoside analogues via Pd-catalyzed Suzuki cross-coupling reaction was hampered by the instability of the TIPDS-protected precursor 6-iodo-2'-deoxyuridine 1 in alkaline media due to cleavage of the glycosidic bond. Herein, the successful application of the Liebeskind reaction under base-free conditions is reported. This method comprises of the stoichiometric use of copper thiophene carboxylate (CuTC) as co-reagent at slightly elevated temperatures. Fluoride-mediated desilylation and Yoshikawa-phosphorylation afforded the nucleotide analogues 4b-c, 4e, and 4i. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.036