N³-Boc-3',5'-O-bis-methoxymethyl-2'-O-methylsulfonyloxy-5-methyluridine | 1414853-73-8

• 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-methoxymethyl-2'-O-methylsulfonyloxy-5-methyluridine
• 英文别名: tert-butyl 3-[(2R,3R,4R,5R)-4-(methoxymethoxy)-5-(methoxymethoxymethyl)-3-methylsulfonyloxyoxolan-2-yl]-5-methyl-2,6-dioxopyrimidine-1-carboxylate
• CAS: 1414853-73-8
• 化学式: C₂₀H₃₂N₂O₁₂S
• 分子量: 524.546
• InChiKey: WRUGPQUMNCWJKY-KCYZZUKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  12

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 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.66h， 生成 N³-Boc-3',5'-O-bis-methoxymethyl-2'-O-methylsulfonyloxy-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.