4-{(1S,2R)-2,3-Dichloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1-trityl-1H-imidazole | 142822-34-2

• 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: 4-{(1S,2R)-2,3-Dichloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1-trityl-1H-imidazole
• 英文别名: [(1S,2R)-2,3-dichloro-1-(1-tritylimidazol-4-yl)propoxy]-(2,3-dimethylbutan-2-yl)-dimethylsilane
• CAS: 142822-34-2
• 化学式: C₃₃H₄₀Cl₂N₂OSi
• 分子量: 579.685
• InChiKey: CZROTGMCUNUHDL-IGYGKHONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.27
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-{(1S,2R)-2,3-Dichloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1-trityl-1H-imidazole 在 叠氮化锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 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
• 作为产物：
  描述：

  (S)-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(1-trityl-1H-imidazol-4-yl)-methanol 在 咪唑 、 四氯化碳 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.0h， 生成 4-{(1S,2R)-2,3-Dichloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1-trityl-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.