1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-methoxyphenyl)pyrimidine-2,4-dione | 1353743-30-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-methoxyphenyl)pyrimidine-2,4-dione
• CAS: 1353743-30-2
• 化学式: C₁₆H₁₈N₂O₆
• 分子量: 334.329
• InChiKey: QKMBFWSYAMOMOR-GZBFAFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-methoxyphenyl)pyrimidine-2,4-dione 在 1,8-双二甲氨基萘 、 三甲氧基磷 、 三氯氧磷 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以33%的产率得到
  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
• 作为产物：
  描述：

  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) 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.75h， 生成 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-methoxyphenyl)pyrimidine-2,4-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

文献信息

• Synthesis of 6-aryl-2′-deoxyuridine nucleosides via a Liebeskind cross-coupling methodology
  作者：Martin Kögler、Steven De Jonghe、Piet Herdewijn

  DOI：10.1016/j.tetlet.2011.11.036

  日期：2012.1

  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.