1-(5-O-tert-butyldimethylsilyl-4-seleno-β-D-ribofuranosyl)uracil | 1030021-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(5-O-tert-butyldimethylsilyl-4-seleno-β-D-ribofuranosyl)uracil
• CAS: 1030021-72-7
• 化学式: C₁₅H₂₆N₂O₅SeSi
• 分子量: 421.427
• InChiKey: OXDFBEWTGGGMEI-OJAKKHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  104.55
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(5-O-tert-butyldimethylsilyl-4-seleno-β-D-ribofuranosyl)uracil 、 N,N'-硫羰基二咪唑 以 氯仿 为溶剂， 以58%的产率得到1-(5-O-tert-butyldimethylsilyl-2,3-O-thiocarbonate-4-seleno-β-D-ribofuranosyl)uracil
  参考文献：
  名称：

  Stereoselective Synthesis and Conformational Study of Novel 2′,3′-Didehydro-2′,3′-dideoxy-4′-selenonucleosides

  摘要：

  Stereoselective synthesis of novel 2',3'-didehydro-2',3'dideoxy-4'-selenonnucleosides (4'-seleno-d4Ns) 4a-c was accomplished via 4'-selenoribofuranosyl pyrimidines 11a-c, as key intermediates. 4'-Selenoribofuranosyl pyrimidines 11a-c were efficiently synthesized from D-ribose or D-gulonic gamma-lactone using a Pummerer-type condensation as a key step. Introduction of 2',3'-double bond was achieved by treating cyclic 2',3'-thiocarbonate with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine.

  DOI：

  10.1021/jo8003277
• 作为产物：
  描述：

  N-1-(4'-seleno-β-D-ribofuranosyl)-uracil 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以65%的产率得到1-(5-O-tert-butyldimethylsilyl-4-seleno-β-D-ribofuranosyl)uracil
  参考文献：
  名称：

  Stereoselective Synthesis and Conformational Study of Novel 2′,3′-Didehydro-2′,3′-dideoxy-4′-selenonucleosides

  摘要：

  Stereoselective synthesis of novel 2',3'-didehydro-2',3'dideoxy-4'-selenonnucleosides (4'-seleno-d4Ns) 4a-c was accomplished via 4'-selenoribofuranosyl pyrimidines 11a-c, as key intermediates. 4'-Selenoribofuranosyl pyrimidines 11a-c were efficiently synthesized from D-ribose or D-gulonic gamma-lactone using a Pummerer-type condensation as a key step. Introduction of 2',3'-double bond was achieved by treating cyclic 2',3'-thiocarbonate with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine.

  DOI：

  10.1021/jo8003277