2,3'-anhydro-5'-O-(4,4'-dimethoxytrityl)thymidine | 191474-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,3'-anhydro-5'-O-(4,4'-dimethoxytrityl)thymidine
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydrothymidine；5'-O-(4,4'-dimethoxytrityl)-2,3-anhydrothymidine；2,3'-anhydro-5'-(4,4'-dimethoxytrityl)thymidine；2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one, 3-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-2,3-dihydro-8-methyl-, (2R,3R,5R)-；(1R,9R,10R)-10-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one
• CAS: 191474-13-2
• 化学式: C₃₁H₃₀N₂O₆
• 分子量: 526.589
• InChiKey: SWDIHODJLJEUEJ-JCYYIGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3'-anhydro-5'-O-(4,4'-dimethoxytrityl)thymidine 在 盐酸 、 potassium fluoride 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 1.02h， 生成 3’-脱氧-3-氟胸苷
  参考文献：
  名称：

  Synthesis of 3′‐deoxy‐3′‐[ ¹⁸ F]fluoro‐thymidine with 2,3′‐anhydro‐5′‐ O ‐(4,4′‐dimethoxytrityl)‐thymidine

  摘要：

  [C-11]Thymidine has been used as a proliferation marker in positron-emission-tomography (PET) studies of tumors. This compound showed metabolite related problems and the radiosynthesis proved to be difficult. Recently, the more stable 3'-deoxy-3'-[F-18]fluorothymidine ([F-18]FLT) has been suggested as an alternative. One advantage of [F-18]FLT is based on thymidine kinase-1 catalyzed phosphorylation of FLT and the intracellular accumulation of this metabolite without participation in DNA synthesis. The radiosynthesis of [F-18]FLT originally designed by Grierson et al. was found to be demanding especially regarding the workup df the [F-18]fluoride/1-(2-deoxy-3 -O-nosyl-5-O-DMT-beta -D-threo-pento-furanosyl)-3-DMBn-thymine reaction mixture. Instead, we us ed 2,3'-anhydro-5'-0-(4,4'-dimethoxytrityl) thymi dine as a precursor for the synthesis of [F-18]FLT. In DMSO at 175 degreesC and in presence of Kryptofix(R) 2.2.2. we obtained 5.6+/-1,4 % [F-18]FLT (EOS).

  DOI：

  10.1002/1099-1344(20001030)43:12<1211::aid-jlcr408>3.0.co;2-#
• 作为产物：
  描述：

  保护胸苷 在 sodium hydroxide