5-Amino-1-(p-methoxybenzyl)-4-<(1'R)-<(2'-azido-1'-tert-butyldimethylsilyl)oxy>ethyl>imidazole | 151256-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-Amino-1-(p-methoxybenzyl)-4-<(1'R)-<(2'-azido-1'-tert-butyldimethylsilyl)oxy>ethyl>imidazole
• CAS: 151256-27-8
• 化学式: C₁₉H₃₀N₆O₂Si
• 分子量: 402.572
• InChiKey: RROPJYBECOZQHI-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  111.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-Amino-1-(p-methoxybenzyl)-4-<(1'R)-<(2'-azido-1'-tert-butyldimethylsilyl)oxy>ethyl>imidazole 在 吡啶 、 1,3-丙二硫醇 、 5A molecular sieve 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 3.17h， 生成 (8R)-6-Acetyl-3-(p-methoxybenzyl)-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
• 作为产物：
  描述：

  (2S,3R)-4-Azido-2-<(tert-butoxycarbonyl)amino>-3-<(tert-butyldimethylsilyl)oxy>butanamide 在 吡啶 、 5A molecular sieve 、 对甲苯磺酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 100.75h， 生成 5-Amino-1-(p-methoxybenzyl)-4-<(1'R)-<(2'-azido-1'-tert-butyldimethylsilyl)oxy>ethyl>imidazole
  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