N³-Boc-3',5'-O-bis-tetrahydropyranyl-2'-O-p-nitrophenylsulfonyl-5-methyluridine | 1414853-79-4

• 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-3',5'-O-bis-tetrahydropyranyl-2'-O-p-nitrophenylsulfonyl-5-methyluridine
• 英文别名: tert-butyl 5-methyl-3-[(2R,3R,4R,5R)-3-(4-nitrophenyl)sulfonyloxy-4-(oxan-2-yloxy)-5-(oxan-2-yloxymethyl)oxolan-2-yl]-2,6-dioxopyrimidine-1-carboxylate
• CAS: 1414853-79-4
• 化学式: C₃₁H₄₁N₃O₁₄S
• 分子量: 711.744
• InChiKey: XOTHLANBBDDRTE-PRKSYZAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  211
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  5-甲基尿甙 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.25h， 生成 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

文献信息

• 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.