N2-benzoyl-7-benzylguanine | 182005-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N2-benzoyl-7-benzylguanine
• 英文别名: N-(7-benzyl-6-oxo-1H-purin-2-yl)benzamide
• CAS: 182005-36-3
• 化学式: C₁₉H₁₅N₅O₂
• 分子量: 345.36
• InChiKey: KROJWQMASJIILC-UHFFFAOYSA-N

物化性质

• 熔点：
  265-267 °C(Solv: water (7732-18-5))
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(乙酰氧基甲基)-4-溴丁基乙酸酯 、 N2-benzoyl-7-benzylguanine 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-N2-benzoyl-7-benzylguaninium bromide
  参考文献：
  名称：

  Process for producing purine derivatives

  摘要：

  在只向嘌呤衍生物的9位引入所需取代基的情况下，首先在通过发酵获得的天然嘌呤核苷酸或其衍生物的嘌呤碱基的7位引入易于去除的取代基，然后水解核糖部分以形成在7位具有取代基的嘌呤衍生物，随后在9位引入所需的取代基，然后去除7位的取代基。

  公开号：

  US05831092A1
• 作为产物：
  描述：

  鸟苷 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium acetate 、 sodium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 N2-benzoyl-7-benzylguanine
  参考文献：
  名称：

  Practical syntheses of penciclovir and famciclovir from N2-acetyl-7-benzylguanine

  摘要：

  We have established practical methods for the synthesis of penciclovir (PCV) and famciclovir (FCV) from readily available guanosine via N2-acetyl-7-benzylguanine. The alkylation of N2-acetyl-7-benzylguanine proceeded selectively at the N9 position to give the desired alkylated product in good yield in salt form. After conventional catalytic hydrogenolysis of the benzyl group and hydrolysis of the resulting acetate, pure PCV was obtained without the need for chromatography. As a side chain precursor, the mesylate was selected rather than a halide since the corresponding halides gave several impurities under the same reaction conditions. Two procedures for the synthesis of FCV from PCV and a derivative are also reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.080

文献信息

• Practical syntheses of penciclovir and famciclovir from N2-acetyl-7-benzylguanine
  作者：Takayoshi Torii、Hiroshi Shiragami、Keizo Yamashita、Yumiko Suzuki、Toyoto Hijiya、Tatsuki Kashiwagi、Kunisuke Izawa

  DOI：10.1016/j.tet.2006.03.080

  日期：2006.6

  We have established practical methods for the synthesis of penciclovir (PCV) and famciclovir (FCV) from readily available guanosine via N2-acetyl-7-benzylguanine. The alkylation of N2-acetyl-7-benzylguanine proceeded selectively at the N9 position to give the desired alkylated product in good yield in salt form. After conventional catalytic hydrogenolysis of the benzyl group and hydrolysis of the resulting acetate, pure PCV was obtained without the need for chromatography. As a side chain precursor, the mesylate was selected rather than a halide since the corresponding halides gave several impurities under the same reaction conditions. Two procedures for the synthesis of FCV from PCV and a derivative are also reported. (c) 2006 Elsevier Ltd. All rights reserved.
• Process for producing purine derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：US05831092A1

  公开（公告）日：1998-11-03

  Purine derivatives in which a desired substituent is introduced into the 9-position only are synthesized by first introducing an easily-removable substituent in the 7-position of a purine base of natural purine nucleosides obtained through fermentation or derivatives thereof, then hydrolyzing the ribose moiety to form purine derivatives having the substituent in the 7-position, subsequently introducing the desired substituent in the 9-position, and then removing the substituent in the 7-position.

  在只向嘌呤衍生物的9位引入所需取代基的情况下，首先在通过发酵获得的天然嘌呤核苷酸或其衍生物的嘌呤碱基的7位引入易于去除的取代基，然后水解核糖部分以形成在7位具有取代基的嘌呤衍生物，随后在9位引入所需的取代基，然后去除7位的取代基。