1-[(4R,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-[1,3]dithiolan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione | 176703-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(4R,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-[1,3]dithiolan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(4R,5R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]-1,3-dithiolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 176703-54-1
• 化学式: C₂₂H₄₂N₂O₄S₂Si₂
• 分子量: 518.889
• InChiKey: MUIVYDRSAAVUIO-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(4R,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-[1,3]dithiolan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到1-((4R,5R)-4,5-Bis-hydroxymethyl-[1,3]dithiolan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of [4,5-Bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides as Potential Inhibitors of HIV¹

  摘要：

  The synthesis of [4,5-bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides is described. (2S,3S)-1,2: 3,4-Diepoxybutane (13) was reacted with potassium thiocyanate to give (2R,3R)-1,2:3,4-diepithiobutane (14). Thiiranering opening with acetate followed by deacetylation gave (2R,3R)-2,3-dithiothreitol (19) which was silylated and treated with trimethyl orthoformate to give the 2-methoxy-1,3-dithiolane 20. Condensation of 20 with silylated thymine, uracil, N-4-benzoylcytosine and 6-chloropurine using a modified Vorbruggen procedure, followed by deprotection, gave the nucleoside analogues. Compounds 26, 28, and 30 were found to be inactive when tested for anti-HIV activity in vitro.

  DOI：

  10.1021/jo952228o
• 作为产物：
  描述：

  (2R,3R)-1,4-bis[[tert-butyl(dimethyl)silyl]oxy]butane-2,3-dithiol 在 ammonium sulfate 、 三甲基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-[(4R,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-[1,3]dithiolan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of [4,5-Bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides as Potential Inhibitors of HIV¹

  摘要：

  The synthesis of [4,5-bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides is described. (2S,3S)-1,2: 3,4-Diepoxybutane (13) was reacted with potassium thiocyanate to give (2R,3R)-1,2:3,4-diepithiobutane (14). Thiiranering opening with acetate followed by deacetylation gave (2R,3R)-2,3-dithiothreitol (19) which was silylated and treated with trimethyl orthoformate to give the 2-methoxy-1,3-dithiolane 20. Condensation of 20 with silylated thymine, uracil, N-4-benzoylcytosine and 6-chloropurine using a modified Vorbruggen procedure, followed by deprotection, gave the nucleoside analogues. Compounds 26, 28, and 30 were found to be inactive when tested for anti-HIV activity in vitro.

  DOI：

  10.1021/jo952228o

文献信息

• Synthesis of [4,5-Bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides as Potential Inhibitors of HIV¹
  作者：Jonas Brånalt、Ingemar Kvarnström、Björn Classon、Bertil Samuelsson

  DOI：10.1021/jo952228o

  日期：1996.1.1

  The synthesis of [4,5-bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides is described. (2S,3S)-1,2: 3,4-Diepoxybutane (13) was reacted with potassium thiocyanate to give (2R,3R)-1,2:3,4-diepithiobutane (14). Thiiranering opening with acetate followed by deacetylation gave (2R,3R)-2,3-dithiothreitol (19) which was silylated and treated with trimethyl orthoformate to give the 2-methoxy-1,3-dithiolane 20. Condensation of 20 with silylated thymine, uracil, N-4-benzoylcytosine and 6-chloropurine using a modified Vorbruggen procedure, followed by deprotection, gave the nucleoside analogues. Compounds 26, 28, and 30 were found to be inactive when tested for anti-HIV activity in vitro.