(2S,3S)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-one | 377748-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-one
• 英文别名: (3aS,6aS)-2,2-dimethyl-6-[(2-methylpropan-2-yl)oxymethyl]-3a,6a-dihydrocyclopenta[d][1,3]dioxol-4-one
• CAS: 377748-55-5
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: BBDQIQRUZZQDHN-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (1'S,2'R,3'S)-9-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]-6-chloropurine
  参考文献：
  名称：

  Enantiomeric Synthesis of d- and l-Cyclopentenyl Nucleosides and Their Antiviral Activity Against HIV and West Nile Virus

  摘要：

  Enantiomeric synthesis Of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-gamma -ribonolactone and D-ribose, respectively. Coupling of 7 with appropriately blocked purine and pyrimidine bases via the Mitsunobu reaction followed by deprotection afforded the target L-(+)-cyclopentenyl nucleosides (24-28, 31, 33, and 36). D-(-)Cyclopentenyl nucleosides (1, 40, 43, and 52-56) were also prepared by a similar procedure for L-isomers from 15. The synthesized compounds were evaluated for their antiviral activity against two RNA viruses: HIV and West Nile virus. Among the synthesized D-(-)-nucleosides, adenine (1, neplanocin A), cytosine (55, CPE-C), and 5-fluorocytosine (56) analogues exhibited moderate to potent anti-HIV activity (EC50 0.1, 0.06, and 5.34 muM, respectively) with significant cytotoxicity in PBM, Vero, and CEM cells. Also, cytosine (55) and 5-fluorocytosine (56) analogues exhibited the most potent anti-West Nile virus activity (EC50 0.2-3.0 and 15-20 muM, respectively). Among L-(+)-nucleosides, only the cytosine (27) analogue exhibited weak anti-HIV activity (EC50 58.9 muM).

  DOI：

  10.1021/jm010256v
• 作为产物：
  描述：

  甲基叔丁基醚 在 吡啶 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 4.5h， 生成 (2S,3S)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-one
  参考文献：
  名称：

  Enantiomeric Synthesis of d- and l-Cyclopentenyl Nucleosides and Their Antiviral Activity Against HIV and West Nile Virus

  摘要：

  Enantiomeric synthesis Of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-gamma -ribonolactone and D-ribose, respectively. Coupling of 7 with appropriately blocked purine and pyrimidine bases via the Mitsunobu reaction followed by deprotection afforded the target L-(+)-cyclopentenyl nucleosides (24-28, 31, 33, and 36). D-(-)Cyclopentenyl nucleosides (1, 40, 43, and 52-56) were also prepared by a similar procedure for L-isomers from 15. The synthesized compounds were evaluated for their antiviral activity against two RNA viruses: HIV and West Nile virus. Among the synthesized D-(-)-nucleosides, adenine (1, neplanocin A), cytosine (55, CPE-C), and 5-fluorocytosine (56) analogues exhibited moderate to potent anti-HIV activity (EC50 0.1, 0.06, and 5.34 muM, respectively) with significant cytotoxicity in PBM, Vero, and CEM cells. Also, cytosine (55) and 5-fluorocytosine (56) analogues exhibited the most potent anti-West Nile virus activity (EC50 0.2-3.0 and 15-20 muM, respectively). Among L-(+)-nucleosides, only the cytosine (27) analogue exhibited weak anti-HIV activity (EC50 58.9 muM).

  DOI：

  10.1021/jm010256v

文献信息

• MODIFIED NUCLEOSIDES, NUCLEOTIDES, AND NUCLEIC ACIDS, AND USES THEREOF
  申请人：modeRNA Therapeutics

  公开号：US20130115272A1

  公开（公告）日：2013-05-09

  The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.
• US9428535B2
  申请人：——

  公开号：US9428535B2

  公开（公告）日：2016-08-30