(8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine | 151256-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑二氮卓类
• 英文名称: (8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine
• 英文别名: tert-butyl (8R)-3-benzyl-8-[tert-butyl(dimethyl)silyl]oxy-7,8-dihydroimidazo[4,5-d][1,3]diazepine-6-carboxylate
• CAS: 151256-36-9
• 化学式: C₂₄H₃₆N₄O₃Si
• 分子量: 456.66
• InChiKey: HTKOTJQEVDEURA-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到(8R)-3-Benzyl-6-(tert-butoxycarbonyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol
  参考文献：
  名称：

  Chirospecific synthesis of the tetrahydroimidazodiazepinol aglycon of pentostatin and its analogs

  摘要：

  A high-yield, versatile method is presented for the stereo- and regiospecific synthesis of the aglycon of pentostatin and its analogues using the L-vinylglycine 1 as the chiral educt. From this four-carbon asymmetric core, containing the contiguous carbons of the target ring system, the synthetic process proceeds with development of the R absolute stereochemistry for the hydroxyl group at C-8 and nitrogen or potential nitrogen functions at the other three carbons. Conversion of the alpha-amino ester to an alpha-amino nitrile is followed by formation of the 1,4,5-trisubstituted aminoimidazole. After generating another amine by reduction of an azide, the diazepine is then annealed by treatment with orthoformate. Using this process, a series of (8R)-8-hydroxy-substituted tetrahydroimidazodiazepinols has been prepared. The protecting group protocol allows specific deprotection at N-3 for subsequent glycosylation and other substitution.

  DOI：

  10.1021/jo00074a041
• 作为产物：
  描述：

  5-Amino-4-<(1'R)-<(2'-azido-1'-tert-butyldimethylsilyl)oxy>ethyl>-1-(2'-cyanoethyl)imidazole 在 1,3-丙二硫醇 、 5A molecular sieve 、 potassium tert-butylate 、 三乙胺 、 三氟乙酸 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.02h， 生成 (8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine
  参考文献：
  名称：

  Chirospecific synthesis of the tetrahydroimidazodiazepinol aglycon of pentostatin and its analogs

  摘要：

  A high-yield, versatile method is presented for the stereo- and regiospecific synthesis of the aglycon of pentostatin and its analogues using the L-vinylglycine 1 as the chiral educt. From this four-carbon asymmetric core, containing the contiguous carbons of the target ring system, the synthetic process proceeds with development of the R absolute stereochemistry for the hydroxyl group at C-8 and nitrogen or potential nitrogen functions at the other three carbons. Conversion of the alpha-amino ester to an alpha-amino nitrile is followed by formation of the 1,4,5-trisubstituted aminoimidazole. After generating another amine by reduction of an azide, the diazepine is then annealed by treatment with orthoformate. Using this process, a series of (8R)-8-hydroxy-substituted tetrahydroimidazodiazepinols has been prepared. The protecting group protocol allows specific deprotection at N-3 for subsequent glycosylation and other substitution.

  DOI：

  10.1021/jo00074a041