(3E)-5-O-tert-butyldimethylsilyl-3-deoxy-1,2-O-isopropylidene-3-(N-methylimino)-α-D-erythro-pentofuranose N-oxide | 175471-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3E)-5-O-tert-butyldimethylsilyl-3-deoxy-1,2-O-isopropylidene-3-(N-methylimino)-α-D-erythro-pentofuranose N-oxide
• CAS: 175471-48-4
• 化学式: C₁₅H₂₉NO₅Si
• 分子量: 331.484
• InChiKey: YZAAWDJKAFXBRA-GLSQKOAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  62.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  乙酸乙酯 、 (3E)-5-O-tert-butyldimethylsilyl-3-deoxy-1,2-O-isopropylidene-3-(N-methylimino)-α-D-erythro-pentofuranose N-oxide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以67%的产率得到<5-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose>-3-spiro-3',2'-methylisoxazolidin-5'-one
  参考文献：
  名称：

  A Novel Type of Spironucleosides: 2′,5′-O-bis-TBDMS Uridine-3′-spiro-3′-isoxazolidin-5′-one and Its Thymidine Congener

  摘要：

  TSAO analogues, 2',5'-O-bis-TBDMS uridine-3'-spiro-3 ''-isoxazolidin-5 ''-on (9) and its thymidine congener 10, as well as model spiro sugar derivatives (3 and 4) have been prepared from the corresponding nitrones through a stereospecific tandem nucleophilic attack. Compounds 9 and 10 which are bioisosters of TSAO-U and T respectively but which lack an amino group on the spiro ring, were found inactive against both HIV-1 and HIV-2.

  DOI：

  10.1080/07328319608002388
• 作为产物：
  描述：

  N-甲基羟胺盐酸盐 、 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到(3E)-5-O-tert-butyldimethylsilyl-3-deoxy-1,2-O-isopropylidene-3-(N-methylimino)-α-D-erythro-pentofuranose N-oxide
  参考文献：
  名称：

  A Novel Type of Spironucleosides: 2′,5′-O-bis-TBDMS Uridine-3′-spiro-3′-isoxazolidin-5′-one and Its Thymidine Congener

  摘要：

  TSAO analogues, 2',5'-O-bis-TBDMS uridine-3'-spiro-3 ''-isoxazolidin-5 ''-on (9) and its thymidine congener 10, as well as model spiro sugar derivatives (3 and 4) have been prepared from the corresponding nitrones through a stereospecific tandem nucleophilic attack. Compounds 9 and 10 which are bioisosters of TSAO-U and T respectively but which lack an amino group on the spiro ring, were found inactive against both HIV-1 and HIV-2.

  DOI：

  10.1080/07328319608002388