(1S,2R,3S,5R)-2-((benzyloxy)methyl)-3-((4-methoxybenzyl)oxy)-6-oxabicyclo[3.1.0]-hexane | 133299-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,3S,5R)-2-((benzyloxy)methyl)-3-((4-methoxybenzyl)oxy)-6-oxabicyclo[3.1.0]-hexane
• 英文别名: (1S,2R,3S,5R)-3-[(4-methoxyphenyl)methoxy]-2-(phenylmethoxymethyl)-6-oxabicyclo[3.1.0]hexane
• CAS: 133299-26-0
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: YEIIUMSXGQPMCC-MHTWAQMVSA-N

物化性质

• 沸点：
  462.4±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,5R)-2-((benzyloxy)methyl)-3-((4-methoxybenzyl)oxy)-6-oxabicyclo[3.1.0]-hexane 在 4-二甲氨基吡啶 、 aluminium(III) iodide 、 偶氮二异丁腈 、 乙二醇甲醚 、 三氟化硼乙醚 、 水 、 三正丁基氢锡 、 lithium hydride 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 13.67h， 生成 (1''R,4''S)-N-<1,9-dihydro-9-(4-acetoxymethylcyclopent-2-enyl)-6-oxopurin-2-yl>acetamide
  参考文献：
  名称：

  Total synthesis of (–)-carbovir

  摘要：

  Optically pure (-)-carbovir has been prepared by two different routes involving stereospecific opening of chiral cyclopentene epoxides by substituted purines. Introduction of the 2',3' unsaturation was accomplished by mesylate elimination, either after introduction of the purine (Route 1), or earlier in the sequence, producing a novel vinyl epoxide (Route 2).

  DOI：

  10.1039/p19910002479
• 作为产物：
  描述：

  (1S,2R,3S,5R)-2-[(苄氧甲基)-6-氧杂二环[3.1.0]己-3-醇 、 4-甲氧基氯苄 在 四丁基碘化铵 、 sodium hydride 作用下， 生成 (1S,2R,3S,5R)-2-((benzyloxy)methyl)-3-((4-methoxybenzyl)oxy)-6-oxabicyclo[3.1.0]-hexane
  参考文献：
  名称：

  Total synthesis of (–)-carbovir

  摘要：

  Optically pure (-)-carbovir has been prepared by two different routes involving stereospecific opening of chiral cyclopentene epoxides by substituted purines. Introduction of the 2',3' unsaturation was accomplished by mesylate elimination, either after introduction of the purine (Route 1), or earlier in the sequence, producing a novel vinyl epoxide (Route 2).

  DOI：

  10.1039/p19910002479

文献信息

• The enantiomers of the 1′,6′-isomer of neplanocin A: Synthesis and antiviral properties
  作者：Wei Ye、Stewart W. Schneller

  DOI：10.1016/j.bmc.2014.07.051

  日期：2014.10

  Both enantiomers of 1′,6′-isoneplanocin have been prepared from a common substituted cyclopentane epoxide in 7 steps. Both compounds were subjected to DNA and RNA viral assessments with moderate to high activity found for both towards human cytomegalovirus, measles, Ebola, norovirus, and dengue. The D-like congener also showed vaccinia and HBV effectiveness. In many of the other antiviral assays both

  1'，6'-异奈普林霉素的两种对映体均由一个常见的取代环戊烷环氧化物经7个步骤制得。对这两种化合物都进行了DNA和RNA病毒评估，发现它们对人巨细胞病毒，麻疹，埃博拉病毒，诺如病毒和登革热均具有中等至高活性。D样同源物还显示出牛痘和HBV有效性。在许多其他抗病毒测定中，两种化合物均显示出细胞毒性，在某些情况下，无法进行EC 50测定。所述š -adenosylhomocysteine水解酶的抑制作用显示了d状目标为等于的neplanocin本身和优于3-deazaneplanocin而像L的类似物，其为13至30倍，比分别3- deazaneplanocin和neplanocin，较少抑制。
• [EN] ENANTIOMERS OF THE 1',6'-ISOMER OF NEPLANOCIN A<br/>[FR] ÉNANTIOMÈRES DE L' 1',6'-ISOMÈRE DE LA NÉPLANOCINE A
  申请人：UNIV AUBURN

  公开号：WO2016022563A1

  公开（公告）日：2016-02-11

  Enantiomers of 1',6'-isoneplanocin, including derivatives of the enantiomers of 1',6'-isoneplanocin, are disclosed along with novel synthetic methods. In particular, a substituted cyclopentane epoxide is synthesized into the enantiomers of 1',6'-isoneplanocin. Enantiomers of carbocyclic nucleoside analogs of 3-deazaneplanocin to provide D- and L-like 1',6'-iso-3-deazaneplanocin are also disclosed. The small molecule chemotherapeutic compounds beneficially provide DNA and RNA antiviral activity, demonstrating activity towards, for example, human cytomegalovirus, measles, Ebola, norovirus, dengue, vaccinia and HBV. Compounds exhibiting reduced S-adenosylhomocysteine hydrolase inhibitory effects are disclosed and provide improved toxicity profiles in comparison to neplanocin. The invention provides improved prophylactic and/or therapeutic antiviral efficacy.

  1',6'-异新平诺西林的对映体，包括1',6'-异新平诺西林对映体的衍生物，以及新颖的合成方法被披露。具体来说，一种取代环戊烷环氧化合物被合成成1',6'-异新平诺西林的对映体。还披露了3-去氮异新平诺西林的碳环核苷类似物的对映体，以提供D-和L-类似的1',6'-异-3-去氮异新平诺西林。这些小分子化疗化合物有益地提供DNA和RNA抗病毒活性，展现出对人类巨细胞病毒、麻疹、埃博拉病毒、诺如病毒、登革热病毒、痘病毒和乙型肝炎病毒等病毒的活性。披露了表现出降低S-腺苷基同型半胱氨酸水解酶抑制作用的化合物，并且与新平诺西林相比，提供了改善的毒性特性。该发明提供了改进的预防和/或治疗抗病毒功效。
• ENANTIOMERS OF THE 1',6'-ISOMER OF NEPLANOCIN A
  申请人：Auburn University

  公开号：US20160039860A1

  公开（公告）日：2016-02-11

  Enantiomers of 1′,6′-isoneplanocin, including derivatives of the enantiomers of 1′,6′-isoneplanocin, are disclosed along with novel synthetic methods. In particular, a substituted cyclopentane epoxide is synthesized into the enantiomers of 1′,6′-isoneplanocin. Enantiomers of carbocyclic nucleoside analogs of 3-deazaneplanocin to provide D- and L-like 1′,6′-iso-3-deazaneplanocin are also disclosed. The small molecule chemotherapeutic compounds beneficially provide DNA and RNA antiviral activity, demonstrating activity towards, for example, human cytomegalovirus, measles, Ebola, norovirus, dengue, vaccinia and HBV. Compounds exhibiting reduced S-adenosylhomocysteine hydrolase inhibitory effects are disclosed and provide improved toxicity profiles in comparison to neplanocin. The invention provides improved prophylactic and/or therapeutic antiviral efficacy.

  本发明涉及1′，6′-异构体的异构体，包括1′，6′-异构体的衍生物，以及新颖的合成方法。具体而言，通过合成取代的环戊烷环氧化物制备1′，6′-异构体。还披露了3-脱氮异异鸟苷类似物的对映体，以提供D-和L-类1′，6′-异-3-脱氮异异鸟苷类似物。这些小分子化疗化合物有益地提供DNA和RNA抗病毒活性，对例如人类巨细胞病毒，麻疹，埃博拉病毒，诺如病毒，登革热，天花和乙型肝炎病毒等具有活性。还披露了表现出较少S-腺苷基同型半胱氨酸水解酶抑制效果的化合物，并与neplanocin相比提供了改进的毒性剖面。本发明提供了改进的预防和/或治疗抗病毒功效。
• Enantiomers of the 1′,6′-isomer of neplanocin A
  申请人：Auburn University

  公开号：US10227373B2

  公开（公告）日：2019-03-12

  Enantiomers of 1′,6′-isoneplanocin, including derivatives of the enantiomers of 1′,6′-isoneplanocin, are disclosed along with novel synthetic methods. In particular, a substituted cyclopentane epoxide is synthesized into the enantiomers of 1′,6′-isoneplanocin. Enantiomers of carbocyclic nucleoside analogs of 3-deazaneplanocin to provide D- and L-like 1′,6′-iso-3-deazaneplanocin are also disclosed. The small molecule chemotherapeutic compounds beneficially provide DNA and RNA antiviral activity, demonstrating activity towards, for example, human cytomegalovirus, measles, Ebola, norovirus, dengue, vaccinia and HBV. Compounds exhibiting reduced S-adenosylhomocysteine hydrolase inhibitory effects are disclosed and provide improved toxicity profiles in comparison to neplanocin. The invention provides improved prophylactic and/or therapeutic antiviral efficacy.

  1′,6′-isoneplanocin 的对映体，包括 1′,6′-isoneplanocin 对映体的衍生物，以及新的合成方法被公开。特别是将取代的环戊烷环氧化物合成为 1′,6′-异柚皮素的对映体。此外，还公开了 3-去氮杂环庚素的碳环核苷类似物的对映体，以提供 D 型和 L 型 1′,6′-异-3-去氮杂环庚素。这些小分子化疗化合物具有良好的 DNA 和 RNA 抗病毒活性，对人类巨细胞病毒、麻疹、埃博拉、诺如病毒、登革热、疫苗和 HBV 等具有活性。本发明公开了具有降低 S-腺苷-高半胱氨酸水解酶抑制作用的化合物，与萘普拉霉素相比，其毒性特征得到了改善。本发明提高了预防性和/或治疗性抗病毒疗效。
• Novel 3′-deoxy analogs of the anti-HBV agent entecavir: synthesis of enantiomers from a single chiral epoxide
  作者：Edward Ruediger、Alain Martel、Nicholas Meanwell、Carola Solomon、Brigitte Turmel

  DOI：10.1016/j.tetlet.2003.11.052

  日期：2004.1

  A synthesis of novel 3'-deoxy analogs of the anti-HBV agent entecavir (BMS-200475) was devised using regioselective ring opening of suitable cyclopentene epoxides as the key step. This versatile approach afforded access to an enantiomeric pair of carbocyclic nucleosides from a single chiral intermediate. (C) 2003 Elsevier Ltd. All rights reserved.