(1S,2S,3R)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-ol | 377748-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3R)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-ol
• 英文别名: (3aR,6S,6aS)-2,2-dimethyl-4-[(2-methylpropan-2-yl)oxymethyl]-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-6-ol
• CAS: 377748-60-2
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: PPXYLZPUTLWLTQ-AXFHLTTASA-N

物化性质

• 沸点：
  328.0±42.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-ol 在 sodium methylate 、 三苯基膦 、 2-巯基乙醇 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 40.0h， 生成 (1'R,2'S,3'R)-9-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]hypoxanthine
  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 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 potassium tert-butylate 、 仲丁基锂 、 potassium carbonate 、 三乙胺 、 对苯醌 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 55.5h， 生成 (1S,2S,3R)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-ol
  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

• Practical Synthesis of <scp>d</scp>- and <scp>l</scp>-2-Cyclopentenone and Their Utility for the Synthesis of Carbocyclic Antiviral Nucleosides against Orthopox Viruses (Smallpox, Monkeypox, and Cowpox Virus)
  作者：Yun H. Jin、Peng Liu、Jianing Wang、Robert Baker、John Huggins、Chung K. Chu

  DOI：10.1021/jo034999v

  日期：2003.11.1

  Highly efficient and practical methodology for the syntheses of D- and l-4,5-O-isopropylidene-2-cyclopentenone (9 and 22), versatile intermediates for the synthesis of carbocyclic nucleosides, have been developed via a ring-closing metathesis reaction from d-ribose in eight steps. The utility of D- and l-4,5-O-isopropylidene-2-cyclopentenone is demonstrated by their application for the preparation

  通过闭环易位反应，开发了用于合成D-和1-4,5-O-异亚丙基-2-环戊烯酮（9和22）（合成碳环核苷的通用中间体）的高效实用方法八个步骤从d-核糖中提取。D-和1-4,5-O-异亚丙基-2-环戊烯酮在制备D-环戊基-6-氮杂嘧啶12和D-环戊烯基-5-卤代胞嘧啶核苷中的应用证明了其实用性（33-35）使用Mitsunobu反应引入嘧啶碱基作为潜在的抗病毒剂。描述了对合成核苷的正痘病毒（天花，猴痘和牛痘病毒）的初步抗病毒活性。