1-(6',6'-dibromo-5',6'-dideoxy-β-D-ribo-5'-hexenofuranosyl)uracil | 64189-20-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 1-(6',6'-dibromo-5',6'-dideoxy-β-D-ribo-5'-hexenofuranosyl)uracil
• 英文别名: 1-(6,6-dibromo-β-D-ribo-5,6-dideoxy-hex-5-enofuranosyl)-1H-pyrimidine-2,4-dione；1-[(2R,3R,4S,5R)-5-(2,2-dibromoethenyl)-3,4-dihydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 64189-20-4
• 化学式: C₁₀H₁₀Br₂N₂O₅
• 分子量: 398.008
• InChiKey: ZHHMHVPQVYVKEW-XCBZGROMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-di-O-acetyl-3-O-benzoyl-6,6-dibromo-5,6-dideoxy-D-ribo-5'-hexenofuranose 在 N,O-双三甲硅基乙酰胺 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 1-(6',6'-dibromo-5',6'-dideoxy-β-D-ribo-5'-hexenofuranosyl)uracil
  参考文献：
  名称：

  Developing an efficient route to the synthesis of nucleoside 1-alkynylphosphonates

  摘要：

  A series of ribonucleoside 1-alkynylphosphonates have been synthesized using a palladium-catalyzed phosphonylation of terminal 1,1-dibromo-1-alkene nucleosidic derivatives and high selectivity for product distribution was observed during this step. Both nucleosidic and osidic pathways were explored and the corresponding optimization study is reported herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.064

文献信息

• Developing an efficient route to the synthesis of nucleoside 1-alkynylphosphonates
  作者：Maïa Meurillon、Franck Gallier、Suzanne Peyrottes、Christian Périgaud

  DOI：10.1016/j.tet.2009.05.064

  日期：2009.8

  A series of ribonucleoside 1-alkynylphosphonates have been synthesized using a palladium-catalyzed phosphonylation of terminal 1,1-dibromo-1-alkene nucleosidic derivatives and high selectivity for product distribution was observed during this step. Both nucleosidic and osidic pathways were explored and the corresponding optimization study is reported herein. (C) 2009 Elsevier Ltd. All rights reserved.