[(3aS,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydroselenopheno[3,4-d][1,3]dioxol-4-yl]methoxy-tert-butyl-dimethylsilane | 1044813-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aS,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydroselenopheno[3,4-d][1,3]dioxol-4-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 1044813-05-9
• 化学式: C₁₄H₂₈O₃SeSi
• 分子量: 351.42
• InChiKey: CUVLYGUOOFWPBS-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3aS,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydroselenopheno[3,4-d][1,3]dioxol-4-yl]methoxy-tert-butyl-dimethylsilane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(3aS,4R,5R,6aR)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydroselenopheno[3,4-d][1,3]dioxole 5-oxide
  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：

  5-O-t-butyldimethylsilyl-2,3-di-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol 在 sodium selenide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 [(3aS,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydroselenopheno[3,4-d][1,3]dioxol-4-yl]methoxy-tert-butyl-dimethylsilane
  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

文献信息

• Stereoselective synthesis of 4′-selenonucleosides using the Pummerer glycosylation reaction
  作者：Kumarasamy Jayakanthan、Blair D. Johnston、B. Mario Pinto

  DOI：10.1016/j.carres.2008.02.014

  日期：2008.7

  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.