[(2R,3R,4R,5R)-5-[4-[(1S,2S)-3-azido-2-chloro-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxypropyl]imidazol-1-yl]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate | 186648-81-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: [(2R,3R,4R,5R)-5-[4-[(1S,2S)-3-azido-2-chloro-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxypropyl]imidazol-1-yl]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 186648-81-7
• 化学式: C₄₀H₄₆ClN₅O₈Si
• 分子量: 788.372
• InChiKey: ZYXIKPSUCYEJKC-SZHFHKCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.71
• 重原子数：
  55
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-[4-[(1S,2S)-3-azido-2-chloro-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxypropyl]imidazol-1-yl]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate 在 盐酸 、 sodium methylate 作用下， 生成 (2R,3R,4S,5R)-2-[4-[(1S,2S)-3-azido-2-chloro-1-hydroxypropyl]imidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol
  参考文献：
  名称：

  New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues

  摘要：

  New C-2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(beta-D-ribofuranosyl)imidazolium 7 and 1-(beta-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared, For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)2 was employed. These new base modified nucleosides were devoid of activity against HIV and cytotoxicity. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00453-3
• 作为产物：
  描述：

  4-{(1S,2S)-3-Azido-2-chloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1H-imidazole 在 氰化汞 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 43.0h， 生成 [(2R,3R,4R,5R)-5-[4-[(1S,2S)-3-azido-2-chloro-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxypropyl]imidazol-1-yl]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues

  摘要：

  New C-2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(beta-D-ribofuranosyl)imidazolium 7 and 1-(beta-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared, For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)2 was employed. These new base modified nucleosides were devoid of activity against HIV and cytotoxicity. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00453-3

文献信息

• New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues
  作者：A. Al Mourabit、M. Beckmann、C. Poupat、A. Ahond、P. Potier

  DOI：10.1016/s0957-4166(96)00453-3

  日期：1996.12

  New C-2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(beta-D-ribofuranosyl)imidazolium 7 and 1-(beta-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared, For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)2 was employed. These new base modified nucleosides were devoid of activity against HIV and cytotoxicity. Copyright (C) 1996 Elsevier Science Ltd.