N³-Boc-2'-O-p-nitrophenylsulfonyl-5-methyluridine | 1414853-72-7

• 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: N³-Boc-2'-O-p-nitrophenylsulfonyl-5-methyluridine
• CAS: 1414853-72-7
• 化学式: C₂₁H₂₅N₃O₁₂S
• 分子量: 543.508
• InChiKey: SHAKDTYJFQNJBZ-YFHUEUNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  206.5
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-吡喃 、 N³-Boc-2'-O-p-nitrophenylsulfonyl-5-methyluridine 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以57%的产率得到N³-Boc-3',5'-O-bis-tetrahydropyranyl-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：

  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 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.25h， 生成 N³-Boc-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