N4-acetyl-1-(5'-O-t-butyldimethylsilyl-2',3'-di-O-isopropylidene-4'-seleno-β-D-ribofuranosyl)-cytosine | 1044813-15-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N4-acetyl-1-(5'-O-t-butyldimethylsilyl-2',3'-di-O-isopropylidene-4'-seleno-β-D-ribofuranosyl)-cytosine
• 英文别名: N⁴-acetyl-1-(5'-O-t-butyldimethylsilyl-2',3'-di-O-isopropylidene-4'-seleno-β-D-ribofuranosyl)-cytosine
• CAS: 1044813-15-1
• 化学式: C₂₀H₃₃N₃O₅SeSi
• 分子量: 502.545
• InChiKey: PNIMSGJPWFKEBT-MWQQHZPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  91.68
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N4-acetyl-1-(5'-O-t-butyldimethylsilyl-2',3'-di-O-isopropylidene-4'-seleno-β-D-ribofuranosyl)-cytosine 在 氨 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Stereoselective synthesis of 4′-selenonucleosides using the Pummerer glycosylation reaction

  摘要：

  The syntheses of four selenonucleosides, namely 4 '-O-selenoadenosine, -cytidine, -thymidine, and -uridine are described. Commercially available D-ribonolactone was converted to the key intermediate 1,4-anhydro-4-seleno-D-ribitol in seven steps in overall excellent yield. Oxidation of the seleno-D-ribitol with MCPBA gave a single diastereomeric selenoxide in excellent yield, which upon Pummerer reaction in the presence of silylated purine or pyrimidine bases gave stereoselectively the corresponding 4'-beta-selenonucleosides. The stereochemistry at the anomeric center was determined by means of 1D-NOE experiments. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.014
• 作为产物：
  描述：

  (3aS,4R,5R,6aR)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydroselenopheno[3,4-d][1,3]dioxole 5-oxide 、 N⁴-acetyl-O-trimethylsilylcytosine 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.25h， 以47%的产率得到N4-acetyl-1-(5'-O-t-butyldimethylsilyl-2',3'-di-O-isopropylidene-4'-seleno-β-D-ribofuranosyl)-cytosine
  参考文献：
  名称：

  Stereoselective synthesis of 4′-selenonucleosides using the Pummerer glycosylation reaction

  摘要：

  The syntheses of four selenonucleosides, namely 4 '-O-selenoadenosine, -cytidine, -thymidine, and -uridine are described. Commercially available D-ribonolactone was converted to the key intermediate 1,4-anhydro-4-seleno-D-ribitol in seven steps in overall excellent yield. Oxidation of the seleno-D-ribitol with MCPBA gave a single diastereomeric selenoxide in excellent yield, which upon Pummerer reaction in the presence of silylated purine or pyrimidine bases gave stereoselectively the corresponding 4'-beta-selenonucleosides. The stereochemistry at the anomeric center was determined by means of 1D-NOE experiments. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.014