(((3aR,5R,6S,6aR)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane | 1620083-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (((3aR,5R,6S,6aR)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane
• CAS: 1620083-08-0
• 化学式: C₅₇H₆₀O₈Si
• 分子量: 901.184
• InChiKey: JIVFWUGWMKYGIH-QNYXGUQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.57
• 重原子数：
  66.0
• 可旋转键数：
  16.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (((3aR,5R,6S,6aR)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 硼烷四氢呋喃络合物 、 2,2,6,6-四甲基哌啶氧化物 、 四丁基氟化铵 、 四丁基溴化铵 、 potassium hydrogencarbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 78.08h， 生成 diethyl (2S,3S,3aR,6aR)-5,5-dimethyl-3-(naphthalen-2-ylmethoxy)-tetrahydrospiro[furo[2,3-d][1,3]dioxole-2,3'-oxolane]-5'-yl phosphonate
  参考文献：
  名称：

  Syntheses of 4′-spirocyclic phosphono-nucleosides as potential inhibitors of hepatitis C virus NS5B polymerase

  摘要：

  To discover novel nucleosides as potential antiviral agents, 4'-spirocyclic phosphono-nucleosides were designed to mimic the monophosphate of R-1479, a known nucleoside inhibitor of HCV NS5B. Bypassing the first kinase step to nucleoside monophosphate is viewed as advantageous since this phosphorylation is often observed as the rate-limiting transformation to the active NTP for many nucleosides. Efficient synthetic routes were developed with a triphenylphosphine-iodine cyclization reaction as the key step to form the tetrahydrofuran 4'-spirocycle. The desired 4'-spirocyclic phosphono-cytidine analogs 12a, 12b, and 16 were prepared in 11 steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.029
• 作为产物：
  描述：

  ((3aR,5R,6S,6aR)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methanol 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 以90%的产率得到(((3aR,5R,6S,6aR)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane
  参考文献：
  名称：

  Syntheses of 4′-spirocyclic phosphono-nucleosides as potential inhibitors of hepatitis C virus NS5B polymerase

  摘要：

  To discover novel nucleosides as potential antiviral agents, 4'-spirocyclic phosphono-nucleosides were designed to mimic the monophosphate of R-1479, a known nucleoside inhibitor of HCV NS5B. Bypassing the first kinase step to nucleoside monophosphate is viewed as advantageous since this phosphorylation is often observed as the rate-limiting transformation to the active NTP for many nucleosides. Efficient synthetic routes were developed with a triphenylphosphine-iodine cyclization reaction as the key step to form the tetrahydrofuran 4'-spirocycle. The desired 4'-spirocyclic phosphono-cytidine analogs 12a, 12b, and 16 were prepared in 11 steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.029