(S)-9-(1-methyl-2-hydroxyethyl)adeninde | 36817-68-2

• 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: (S)-9-(1-methyl-2-hydroxyethyl)adeninde
• 英文别名: (S)-2-(6-amino-9H-purin-9-yl)propan-1-ol；(2S)-2-(6-aminopurin-9-yl)propan-1-ol
• CAS: 36817-68-2
• 化学式: C₈H₁₁N₅O
• 分子量: 193.208
• InChiKey: NMBLSWKTQBVMBR-YFKPBYRVSA-N

物化性质

• 沸点：
  448.5±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-9-(1-methyl-2-hydroxyethyl)adeninde 在 sodium hydroxide 、 三甲基溴硅烷 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (S)-9-(1-methyl-2-phosphonomethoxyethyl)adeninde sodium salt
  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：

  (S)-2-[(5-amino-6-chloropyrimidin-4-yl)amino]-1-propanol 在 盐酸 、 氨 作用下， 以 甲醇 为溶剂， 生成 (S)-9-(1-methyl-2-hydroxyethyl)adeninde
  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

• 一种合成替诺福韦类似物的方法
  申请人：河南师范大学

  公开号：CN109369720B

  公开（公告）日：2020-10-16

  本发明公开了一种合成替诺福韦类似物的方法，属于医药中间体合成技术领域。采用α‑嘌呤取代羧酸1和醇2为原料，加入溶剂、碱、酸酐，以手性(S)‑BTM为催化剂，反应后得到手性非环嘌呤核苷3，反应的对映选择性好，收率中等至优秀。手性非环嘌呤核苷3在硼氢化钠条件下还原得到手性单醇非环嘌呤核苷4，接着磷酸化反应生成替诺福韦类似物5。本发明原料易得，操作简单，为替诺福韦(Tenofovir)类似物的合成提供了一种新途径。
• Dynamic Kinetic Resolution of α-Purine Substituted Alkanoic Acids: Access to Chiral Acyclic Purine Nucleosides
  作者：Huifang Zhang、Mingsheng Xie、Guirong Qu、Junbiao Chang

  DOI：10.1021/acs.orglett.8b03555

  日期：2019.1.4

  An efficient route to construct chiral acyclic purine nucleoside analogues via dynamic kinetic resolution of α-purine substituted alkanoic acids is reported. Using (S)-BTM as the catalyst, diverse chiral acyclic purine nucleoside analogues were obtained in moderate to good yields (up to 93%) and high enantioselectivities (up to 98% ee). Chiral acyclic purine nucleosides could be obtained from the esterified

  报道了通过α-嘌呤取代的链烷酸的动态动力学拆分来构建手性无环嘌呤核苷类似物的有效途径。使用（S）-BTM作为催化剂，可以以中等至良好的收率（高达93％）和高的对映选择性（高达98％ee）获得各种手性无环嘌呤核苷类似物。可以通过还原反应从酯化产物中获得手性无环嘌呤核苷，然后将其转移到替诺福韦类似物中。
• 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.