4-{(1S,2S)-3-Azido-2-chloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1H-imidazole | 142822-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-{(1S,2S)-3-Azido-2-chloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1H-imidazole
• 英文别名: [(1S,2S)-3-azido-2-chloro-1-(1H-imidazol-5-yl)propoxy]-(2,3-dimethylbutan-2-yl)-dimethylsilane
• CAS: 142822-37-5
• 化学式: C₁₄H₂₆ClN₅OSi
• 分子量: 343.932
• InChiKey: DCHSMVHHHDPQCU-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-{(1S,2S)-3-Azido-2-chloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1-trityl-1H-imidazole 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 以82%的产率得到4-{(1S,2S)-3-Azido-2-chloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1H-imidazole
  参考文献：
  名称：

  Synthèse stéréosélective de la girolline

  摘要：

  Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereoisomeric derivatives have been separated. The stereoselective synthesis of chiral natural girolline has been achieved from D(-)arabinose: this ose is condensed with formamidine acetate to obtain a 4(5)-[1',2',3'-trihydroxypropyl]-imidazole; the side-chain is chlorinated before being aminated via an azido compound and the 2-amino group of girolline is obtained by rhodium catalytic reduction of the 2-diazo derivative.

  DOI：

  10.1016/s0040-4020(01)80443-9

文献信息

• Synthèse stéréosélective de la girolline
  作者：Alain Ahond、Ali Al Mourabit、Manuel Bedoya-Zurita、Richard Heng、Raquel Marques Braga、Christiane Poupat、Pierre Potier

  DOI：10.1016/s0040-4020(01)80443-9

  日期：1992.1

  Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereoisomeric derivatives have been separated. The stereoselective synthesis of chiral natural girolline has been achieved from D(-)arabinose: this ose is condensed with formamidine acetate to obtain a 4(5)-[1',2',3'-trihydroxypropyl]-imidazole; the side-chain is chlorinated before being aminated via an azido compound and the 2-amino group of girolline is obtained by rhodium catalytic reduction of the 2-diazo derivative.
• 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.