2-acetyl-7-benzyl-9-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]guaninium inner salt | 204515-22-0

• 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: 2-acetyl-7-benzyl-9-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]guaninium inner salt
• CAS: 204515-22-0
• 化学式: C₂₂H₂₃N₅O₆
• 分子量: 453.455
• InChiKey: FQQPJGBIQLGXEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  136.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-7-benzyl-9-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]guaninium inner salt 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 氢气 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 40.0~60.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 penciclovir
  参考文献：
  名称：

  Improved Industrial Syntheses of Penciclovir and Famciclovir Using N2-Acetyl-7-Benzylguanine and a Cyclic Side Chain Precursor

  摘要：

  We have established practical synthetic methods for penciclovir (PCV, 1) and famciclovir (FCV, 2) from N2-acetyl-7-benzylguanine (NAc7BnG, 3) and 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (4)-the latter being a more easily prepared cyclic precursor of the diacetate side chain (5) used in the conventional process. The coupling of 4 with 3 proceeded regioselectively at the N9 position of guanine in good yield. The coupling product was then successfully transformed into the known antiviral agents in a short number of steps.

  DOI：

  10.1080/15257770600686279
• 作为产物：
  描述：

  N²-acetyl-7-benzylguanine 、 1,1-环丙烷二甲酸环异亚丙酯 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以74%的产率得到2-acetyl-7-benzyl-9-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]guaninium inner salt
  参考文献：
  名称：

  Improved Industrial Syntheses of Penciclovir and Famciclovir Using N2-Acetyl-7-Benzylguanine and a Cyclic Side Chain Precursor

  摘要：

  We have established practical synthetic methods for penciclovir (PCV, 1) and famciclovir (FCV, 2) from N2-acetyl-7-benzylguanine (NAc7BnG, 3) and 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (4)-the latter being a more easily prepared cyclic precursor of the diacetate side chain (5) used in the conventional process. The coupling of 4 with 3 proceeded regioselectively at the N9 position of guanine in good yield. The coupling product was then successfully transformed into the known antiviral agents in a short number of steps.

  DOI：

  10.1080/15257770600686279

文献信息

• An Economical Synthesis of Famciclovir
  作者：Toyoto Hijiya、Keizo Yamashita、Mitsuhiko Kojima、Yumiko Uchida、Satoshi Katayama、Takayoshi Torii、Hiroshi Shiragami、Kunisuke Izawa

  DOI：10.1080/15257779908041530

  日期：1999.4

  An economical synthesis of famciclovir from N-2-acetyl-7-benzylguanine by a novel regioselective alkylation with the diester cyclopropane compound was developed.