(1R,2R)-9-(1-hydroxymethyl-2-hydroxypropyl)adenine | 295324-23-1

• 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: (1R,2R)-9-(1-hydroxymethyl-2-hydroxypropyl)adenine
• 英文别名: (2R,3R)-2-(6-aminopurin-9-yl)butane-1,3-diol
• CAS: 295324-23-1
• 化学式: C₉H₁₃N₅O₂
• 分子量: 223.235
• InChiKey: BUNYMGKOUFWXHH-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R)-9-(1-hydroxymethyl-2-hydroxypropyl)adenine 在 4-二甲氨基吡啶 、 三乙胺 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Synthesis of Acyclic Nucleoside and Nucleotide Analogues from Amino Acids: A Convenient Approach to a PMEA–PMPA Hybrid

  摘要：

  Nonracemic amino alcohols derived from common amino acids have been used to assemble acyclic nucleoside and nucleotide analogues with control of absolute stereochemistry. Both (R)- and (S)-2-amino-1-propanol, readily available from D- or L-alanine, were used to prepare the nucleoside analogues (R)- and (S)-9-[1-methyl-2-hydroxyethyl]adenine, and then the nucleotide analogues (R)- and (S)-9-[1-methyl-2-phosphonomethoxyethyl] adenine. In a similar fashion, the CBz derivative of L-threonine was used to prepare first (1R,2R)-9-[1-hydroxymethyl-2-hydroxypropyl]adenine, and then the bis phosphonomethoxy derivative. The bis phosphonate derived from threonine represents a unique structural hybrid of PMEA and PMPA, both of which have well established antiviral activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00422-1
• 作为产物：
  描述：

  (2R,3R)-2-[(5-amino-6-chloropyrimidin-4-yl)amino]-1,3-butanediol 在 盐酸 、 氨 作用下， 以 乙醇 为溶剂， 反应 53.0h， 生成 (1R,2R)-9-(1-hydroxymethyl-2-hydroxypropyl)adenine
  参考文献：
  名称：

  Synthesis of Acyclic Nucleoside and Nucleotide Analogues from Amino Acids: A Convenient Approach to a PMEA–PMPA Hybrid

  摘要：

  Nonracemic amino alcohols derived from common amino acids have been used to assemble acyclic nucleoside and nucleotide analogues with control of absolute stereochemistry. Both (R)- and (S)-2-amino-1-propanol, readily available from D- or L-alanine, were used to prepare the nucleoside analogues (R)- and (S)-9-[1-methyl-2-hydroxyethyl]adenine, and then the nucleotide analogues (R)- and (S)-9-[1-methyl-2-phosphonomethoxyethyl] adenine. In a similar fashion, the CBz derivative of L-threonine was used to prepare first (1R,2R)-9-[1-hydroxymethyl-2-hydroxypropyl]adenine, and then the bis phosphonomethoxy derivative. The bis phosphonate derived from threonine represents a unique structural hybrid of PMEA and PMPA, both of which have well established antiviral activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00422-1

文献信息

• Synthesis of Acyclic Nucleoside and Nucleotide Analogues from Amino Acids: A Convenient Approach to a PMEA–PMPA Hybrid
  作者：Arlen L Jeffery、Jae-Hun Kim、David F Wiemer

  DOI：10.1016/s0040-4020(00)00422-1

  日期：2000.7

  Nonracemic amino alcohols derived from common amino acids have been used to assemble acyclic nucleoside and nucleotide analogues with control of absolute stereochemistry. Both (R)- and (S)-2-amino-1-propanol, readily available from D- or L-alanine, were used to prepare the nucleoside analogues (R)- and (S)-9-[1-methyl-2-hydroxyethyl]adenine, and then the nucleotide analogues (R)- and (S)-9-[1-methyl-2-phosphonomethoxyethyl] adenine. In a similar fashion, the CBz derivative of L-threonine was used to prepare first (1R,2R)-9-[1-hydroxymethyl-2-hydroxypropyl]adenine, and then the bis phosphonomethoxy derivative. The bis phosphonate derived from threonine represents a unique structural hybrid of PMEA and PMPA, both of which have well established antiviral activity. (C) 2000 Elsevier Science Ltd. All rights reserved.