1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-2,3-didehydro-4-seleno-β-D-ribofuranosyl)uracil | 1030021-76-1

• 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-2,3-dideoxy-2,3-didehydro-4-seleno-β-D-ribofuranosyl)uracil
• 英文别名: 1-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,5-dihydroselenophen-2-yl]pyrimidine-2,4-dione
• CAS: 1030021-76-1
• 化学式: C₁₅H₂₄N₂O₃SeSi
• 分子量: 387.413
• InChiKey: SNIMCVMVYPURBM-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-2,3-didehydro-4-seleno-β-D-ribofuranosyl)uracil 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以80%的产率得到1-(2,3-dideoxy-2,3-didehydro-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：

  1-(5-O-tert-butyldimethylsilyl-2,3-O-thiocarbonate-4-seleno-β-D-ribofuranosyl)uracil 在 1,3-二甲基-2-苯基-2-磷杂咪唑烷 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-2,3-didehydro-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

文献信息

• Stereoselective Synthesis and Conformational Study of Novel 2′,3′-Didehydro-2′,3′-dideoxy-4′-selenonucleosides
  作者：Dilip K. Tosh、Won Jun Choi、Hea Ok Kim、Yoonji Lee、Shantanu Pal、Xiyan Hou、Jungwon Choi、Sun Choi、Lak Shin Jeong

  DOI：10.1021/jo8003277

  日期：2008.6.1

  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.