1-[(6aR,8R,9R,9aR)-2,2,4,4-tetra(propan-2-yl)-9-trimethylsilyloxy-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methylpyrimidine-2,4-dione | 1266095-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(6aR,8R,9R,9aR)-2,2,4,4-tetra(propan-2-yl)-9-trimethylsilyloxy-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1266095-78-6
• 化学式: C₂₅H₄₈N₂O₇Si₃
• 分子量: 572.922
• InChiKey: HPBJXGMLASQVKF-GBEXAXCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(6aR,8R,9R,9aR)-2,2,4,4-tetra(propan-2-yl)-9-trimethylsilyloxy-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 N³-Boc-3',5'-O-1,1,3,3-tetraisopropyl-1,3-disiloxane-2'-O-p-nitrophenylsulfonyl-5-methyluridine
  参考文献：
  名称：

  An investigation on stereospecific fluorination at the 2′-arabino-position of a pyrimidine nucleoside: radiosynthesis of 2′-deoxy-2′-[18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil

  摘要：

  Direct fluorination at the 2'-arabino-position of a pyrimidine nucleoside has been a long-standing challenge, yet we recently reported such a stereospecific fluorination for the first time in the synthesis of [F-18]FMAU, albeit in low yields. Herein we report the results of an investigation on stereospecific fluorination on a variety of precursors for synthesis of [F-18]FMAU. Several precursors were synthesized in multiple steps and fluorination was performed at the 2'-arabino-position using K[F-18]/kryptofix 2.2.2. All precursors produced [F-18]FMAU in low yields. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.10.001
• 作为产物：
  描述：

  5-甲基尿甙 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(6aR,8R,9R,9aR)-2,2,4,4-tetra(propan-2-yl)-9-trimethylsilyloxy-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  在嘧啶核苷的 2'-阿拉伯位置进行立体有择氟化的新方法：[18F]-FMAU 的合成

  摘要：

  嘧啶核苷在 2'-阿拉伯位置的直接氟化被认为是极其困难的，如果不是不可能的话。2'-deoxy-2'-fluoro-5-methy-1-β-D-arabinofuranosyluracil (FMAU) 及其 5-取代类似物的常规合成涉及 1,3,5-tri-O-苯甲酰基的立体定向氟化-α-D-呋喃核糖-2-磺酸酯，然后在 C1 位进行溴化，然后与嘧啶-双-三甲基甲硅烷基醚偶联。根据这种方法开发了几种放射性标记的核苷类似物，包括 [ 18 F] FMAU 和其他 5 取代的类似物。然而，使用这种多步骤方法常规生产这些化合物是不方便的并且限制了它们的临床应用。我们开发了一种新的前体和方法，用于在 2'-阿拉伯位置直接氟化预先形成的核苷类似物，通过[18F]FMAU的放射合成举例说明。2'-methylsulfonyl-3',5'-O-tetrahydropyranyl-N3-Boc-5-me

  DOI：

  10.1002/jlcr.1797

文献信息

• A novel method for stereospecific fluorination at the 2′-arabino-position of pyrimidine nucleoside: synthesis of [18F]-FMAU
  作者：Nashaat Turkman、Juri G. Gelovani、Mian M. Alauddin

  DOI：10.1002/jlcr.1797

  日期：2010.11

  produced the desired [18F]FMAU. The average radiochemical yield was 2.0% (decay corrected, n=6), from the end of bombardment. Radiochemical purity was >99%, and specific activity was >1800 mCi/µmol. Synthesis time was 95–100 min from the end of bombardment. This direct fluorination is a novel method for synthesis of [18F]FMAU, and the method should be suitable for production of other 5-substituted pyrimidine

  嘧啶核苷在 2'-阿拉伯位置的直接氟化被认为是极其困难的，如果不是不可能的话。2'-deoxy-2'-fluoro-5-methy-1-β-D-arabinofuranosyluracil (FMAU) 及其 5-取代类似物的常规合成涉及 1,3,5-tri-O-苯甲酰基的立体定向氟化-α-D-呋喃核糖-2-磺酸酯，然后在 C1 位进行溴化，然后与嘧啶-双-三甲基甲硅烷基醚偶联。根据这种方法开发了几种放射性标记的核苷类似物，包括 [ 18 F] FMAU 和其他 5 取代的类似物。然而，使用这种多步骤方法常规生产这些化合物是不方便的并且限制了它们的临床应用。我们开发了一种新的前体和方法，用于在 2'-阿拉伯位置直接氟化预先形成的核苷类似物，通过[18F]FMAU的放射合成举例说明。2'-methylsulfonyl-3',5'-O-tetrahydropyranyl-N3-Boc-5-me
• An investigation on stereospecific fluorination at the 2′-arabino-position of a pyrimidine nucleoside: radiosynthesis of 2′-deoxy-2′-[18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil
  作者：Nashaat Turkman、Vincenzo Paolillo、Juri G. Gelovani、Mian M. Alauddin

  DOI：10.1016/j.tet.2012.10.001

  日期：2012.12

  Direct fluorination at the 2'-arabino-position of a pyrimidine nucleoside has been a long-standing challenge, yet we recently reported such a stereospecific fluorination for the first time in the synthesis of [F-18]FMAU, albeit in low yields. Herein we report the results of an investigation on stereospecific fluorination on a variety of precursors for synthesis of [F-18]FMAU. Several precursors were synthesized in multiple steps and fluorination was performed at the 2'-arabino-position using K[F-18]/kryptofix 2.2.2. All precursors produced [F-18]FMAU in low yields. (C) 2012 Published by Elsevier Ltd.