(5-Ethoxy-4-trimethylsilyloxypyrimidin-2-yl)sulfanyl-trimethylsilane | 141917-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-Ethoxy-4-trimethylsilyloxypyrimidin-2-yl)sulfanyl-trimethylsilane
• CAS: 141917-03-5
• 化学式: C₁₂H₂₄N₂O₂SSi₂
• 分子量: 316.572
• InChiKey: MRTHNILVEJHFSO-UHFFFAOYSA-N

物化性质

• 沸点：
  357.8±52.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5-Ethoxy-4-trimethylsilyloxypyrimidin-2-yl)sulfanyl-trimethylsilane 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 生成 1-(3-azido-2,3-dideoxy-α-D-erythro-pentofuranosyl)-5-ethoxy-2-thiouracil
  参考文献：
  名称：

  New route for the synthesis of 2-thiouracil analogues of 3?-azido-2?,3?-dideoxy nucleosides

  摘要：

  Reaction of 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-erythro-pentofuranoside(5) with silylated 2-thiouracil and 5-alkoxy-2-thiouracils in the presence of trimethylsilyl trifluoromethanesulfonate afforded an anomeric mixture of the corresponding 3'-azido-2',3'-dideoxy-2-thiouridine derivatives with the alpha-anomer as the main product. Deprotected nucleosides were obtained by treatment with tetrabutylammonium fluoride.

  DOI：

  10.1007/bf00810948
• 作为产物：
  描述：

  2-thio-5-ethoxyuracil 、 六甲基二硅氮烷 在 amino sulphate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 (5-Ethoxy-4-trimethylsilyloxypyrimidin-2-yl)sulfanyl-trimethylsilane
  参考文献：
  名称：

  New route for the synthesis of 2-thiouracil analogues of 3?-azido-2?,3?-dideoxy nucleosides

  摘要：

  Reaction of 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-erythro-pentofuranoside(5) with silylated 2-thiouracil and 5-alkoxy-2-thiouracils in the presence of trimethylsilyl trifluoromethanesulfonate afforded an anomeric mixture of the corresponding 3'-azido-2',3'-dideoxy-2-thiouridine derivatives with the alpha-anomer as the main product. Deprotected nucleosides were obtained by treatment with tetrabutylammonium fluoride.

  DOI：

  10.1007/bf00810948

文献信息

• New route for the synthesis of 2-thiouracil analogues of 3?-azido-2?,3?-dideoxy nucleosides
  作者：Abdel Moneim El-Torgoman、Mohammed S. Motawia、Ulla Kj�rsgaard、Erik B. Pedersen

  DOI：10.1007/bf00810948

  日期：1992.4

  Reaction of 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-erythro-pentofuranoside(5) with silylated 2-thiouracil and 5-alkoxy-2-thiouracils in the presence of trimethylsilyl trifluoromethanesulfonate afforded an anomeric mixture of the corresponding 3'-azido-2',3'-dideoxy-2-thiouridine derivatives with the alpha-anomer as the main product. Deprotected nucleosides were obtained by treatment with tetrabutylammonium fluoride.