2-{[2-(乙酰基氨基)-9H-嘌呤-9-基]甲氧基}乙基乙酸酯 | 120356-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-{[2-(乙酰基氨基)-9H-嘌呤-9-基]甲氧基}乙基乙酸酯
• 英文名称: N²,O-diacetyldeoxyacyclovir
• 英文别名: 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine；2-[(2-Acetamidopurin-9-yl)methoxy]ethyl acetate
• CAS: 120356-09-4
• 化学式: C₁₂H₁₅N₅O₄
• 分子量: 293.282
• InChiKey: NZSQZKSAMAZAEC-UHFFFAOYSA-N

物化性质

• 熔点：
  134 °C
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-{[2-(乙酰基氨基)-9H-嘌呤-9-基]甲氧基}乙基乙酸酯 在 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以84%的产率得到N²-acetyldeoxyacyclovir
  参考文献：
  名称：

  A Novel Palladium-Catalyzed Deoxygenation of GuanineO⁶-Arenesulfonates. A Practicable Synthesis of 2-Aminopurine Nucleosides and Related Analogs

  摘要：

  A simple synthesis of 2-aminopurine nucleosides and related derivatives has been accomplished from the corresponding guanine O-6-arenesulfonates. Studies towards the determination of optimum conditions for reduction and regioselectivity control are also reported.

  DOI：

  10.1080/15257779408013268
• 作为产物：
  描述：

  9-((2-acetoxyethoxy)methyl)-2-acetylamino-6-(2,4,6-trimethylbenzenesulfonyloxy)-9H-purine 在 palladium on activated charcoal 、 Lindlar's catalyst 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0~75.0 ℃ 、310.0 kPa 条件下， 反应 27.5h， 生成 2-{[2-(乙酰基氨基)-9H-嘌呤-9-基]甲氧基}乙基乙酸酯
  参考文献：
  名称：

  A Novel Palladium-Catalyzed Deoxygenation of GuanineO⁶-Arenesulfonates. A Practicable Synthesis of 2-Aminopurine Nucleosides and Related Analogs

  摘要：

  A simple synthesis of 2-aminopurine nucleosides and related derivatives has been accomplished from the corresponding guanine O-6-arenesulfonates. Studies towards the determination of optimum conditions for reduction and regioselectivity control are also reported.

  DOI：

  10.1080/15257779408013268

文献信息

• A New Synthesis of Acyclovir Prodrugs.<i>N</i> ²-Acetylacyclovir and 6-Deoxyacyclovir
  作者：Anton Štimac、Jože Kobe

  DOI：10.1055/s-1990-26904

  日期：——

  9-(2-Acetoxyethoxy)-2-amino-1,9-dihydro-6H-purin-6-one (1b) and 2-acetylamino-9-(2-hydroxyethoxy)methyl-1,9-dihydro-6H-purin-6-one (N2-acetylacyclovir 3) were prepared from 9-[(2-acetoxyethoxy)methyl] -2-acetylamino-1,9-dihydro-6H-purin-6-one (1a) using regioselective deacetylation procedures. Compounds 1a and 1b were chlorinated with phosphoryl chloride to give 9-[(2-acetoxyethoxy)methyl]-2-acetylamino-6-chloro-9H-purine (4a) and its N2-deacetylated counterpart (4b), respectively. Subsequent reductive dechlorination of 4a and 4b under conditions of catalytic transfer hydrogenolysis followed by deprotection afforded 6-deoxy-acyclovir (7) in a good overall yield.

  9-(2-乙酰氧基乙氧基)-2-氨基-1,9-二氢-6H-嘌呤-6-酮(1b)和 2-乙酰氨基-9-(2-羟基乙氧基)甲基-1、9-[(2-acetoxyethoxy)methyl] -2-乙酰氨基-1,9-二氢-6H-嘌呤-6-酮 (1a)采用区域选择性脱乙酰化程序制备出 9-[(2-乙酰氧基乙氧基)甲基] -2-乙酰氨基-1,9-二氢-6H-嘌呤-6-酮 (N2-acetylacyclovir 3)。化合物 1a 和 1b 经磷酰氯氯化后，分别得到 9-[(2-乙酰氧乙氧基)甲基]-2-乙酰氨基-6-氯-9H-嘌呤（4a）及其 N2-脱乙酰基对应物（4b）。随后在催化转移氢解条件下对 4a 和 4b 进行还原脱氯，再进行脱保护处理，可得到 6-脱氧-阿昔洛韦（7），总收率很高。
• Process for preparing purine derivatives and novel purine derivatives
  申请人：KRKA, tovarna zdravil, n.sol.o

  公开号：EP0564006A2

  公开（公告）日：1993-10-06

  There are disclosed purine derivatives of the general formula I wherein Z = H, R1 =CH3CO and R3 = H and further N2-acetyl-9-(2-hydroxyethoxymethyl)guanine also being a compound of the formula I. The preparation of these compounds is also disclosed.

  公开了通式 I 的嘌呤衍生物 其中 Z＝H，R1＝CH3CO，R3＝H，此外，N2-乙酰基-9-(2-羟乙氧甲基)鸟嘌呤也是式 I 的化合物。还公开了这些化合物的制备方法。
• Process for preparing purine derivates
  申请人：KEMIJSKI INSTITUT

  公开号：EP0289992B1

  公开（公告）日：1994-04-27
• STIMAC, ANTON;KOBE, JOZE, LAB. MICROCOMPUT., 9,(1990) N, C. 461-464
  作者：STIMAC, ANTON、KOBE, JOZE

  DOI：——

  日期：——
• A Novel Palladium-Catalyzed Deoxygenation of Guanine<i>O</i>⁶-Arenesulfonates. A Practicable Synthesis of 2-Aminopurine Nucleosides and Related Analogs
  作者：Anton Štimac、Darja Muhič、Jože Kobe

  DOI：10.1080/15257779408013268

  日期：1994.3

  A simple synthesis of 2-aminopurine nucleosides and related derivatives has been accomplished from the corresponding guanine O-6-arenesulfonates. Studies towards the determination of optimum conditions for reduction and regioselectivity control are also reported.