uridine 5'-diphospho-α-D-fucofuranose

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: uridine 5'-diphospho-α-D-fucofuranose
• 英文别名: [(2R,3R,4R,5S)-3,4-dihydroxy-5-[(1R)-1-hydroxyethyl]tetrahydrofuran-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] hydrogen phosphate；[(2R,3R,4R,5S)-3,4-dihydroxy-5-[(1R)-1-hydroxyethyl]oxolan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] phosphate
• 化学式: C₁₅H₂₂N₂O₁₆P₂
• 分子量: 548.291
• InChiKey: RYQDVONYCXFOMC-SIAUPFDVSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  277
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  尿苷-5’-二磷酸 、 2-benzimidazolyl 1-thio-β-D-fucofuranoside 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 uridine 5'-diphospho-β-D-fucofuranose 、 uridine 5'-diphospho-α-D-fucofuranose
  参考文献：
  名称：

  Versatile Synthesis of Rare Nucleotide Furanoses

  摘要：

  Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphosphofuranoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.

  DOI：

  10.1021/ol702392x

文献信息

• Versatile Synthesis of Rare Nucleotide Furanoses
  作者：Pauline Peltier、Richard Daniellou、Caroline Nugier-Chauvin、Vincent Ferrières

  DOI：10.1021/ol702392x

  日期：2007.12.1

  Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphosphofuranoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.