1-[(2-deoxy-β-D-erythro-pentofuranosyl)-5-(tert-butyldiphenylsilyl)]-5-(tert-butyldiphenylsilyloxyethyl)-1H,3H-pyrimidin-2,4-dione | 1338780-34-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(2-deoxy-β-D-erythro-pentofuranosyl)-5-(tert-butyldiphenylsilyl)]-5-(tert-butyldiphenylsilyloxyethyl)-1H,3H-pyrimidin-2,4-dione
• CAS: 1338780-34-9
• 化学式: C₄₃H₅₂N₂O₆Si₂
• 分子量: 749.067
• InChiKey: LHXFQAOVNJWUMY-LCKTVPPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  53.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102.78
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-[(2-deoxy-β-D-erythro-pentofuranosyl)-5-(tert-butyldiphenylsilyl)]-5-(tert-butyldiphenylsilyloxyethyl)-1H,3H-pyrimidin-2,4-dione 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 diisopropylammonium tetrazolide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70.4%的产率得到1-[(2-deoxy-β-D-erythro-pentofuranosyl)-5-(tert-butyldiphenylsilyl)]-5-(tert-butyldiphenylsilyloxyethyl)-1H,3H-pyrimidin-2,4-dione 3'-[(2-cyanoethyl) N,N-diisopropylphosphoramidite]
  参考文献：
  名称：

  d(TGGGAG) with 5′-nucleobase-attached large hydrophobic groups as potent inhibitors for HIV-1 envelop proteins mediated cell–cell fusion

  摘要：

  The Hotoda's sequence substituted with TBDPS via 5'-end nucleobase existed as parallel quadruplex structure and exhibited inhibitory activities in an HIV-1 envelop proteins mediated cell-cell fusion assay. This result demonstrated that the 5'-aromatic groups of the Hotoda's sequence are allowed to have a large spatial freedom and remain to be optimized for its role in the binding to HIV-1 envelop proteins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.007
• 作为产物：
  描述：

  1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-(2-tert-butyldiphenylsilyloxyethyl)-1H,3H-pyrimidine-2,4-dione 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64.4%的产率得到1-[(2-deoxy-β-D-erythro-pentofuranosyl)-5-(tert-butyldiphenylsilyl)]-5-(tert-butyldiphenylsilyloxyethyl)-1H,3H-pyrimidin-2,4-dione
  参考文献：
  名称：

  d(TGGGAG) with 5′-nucleobase-attached large hydrophobic groups as potent inhibitors for HIV-1 envelop proteins mediated cell–cell fusion

  摘要：

  The Hotoda's sequence substituted with TBDPS via 5'-end nucleobase existed as parallel quadruplex structure and exhibited inhibitory activities in an HIV-1 envelop proteins mediated cell-cell fusion assay. This result demonstrated that the 5'-aromatic groups of the Hotoda's sequence are allowed to have a large spatial freedom and remain to be optimized for its role in the binding to HIV-1 envelop proteins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.007