1-{(1R,5R,7R,8S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-8-hydroxy-6-oxa-bicyclo[3.2.1]oct-3-en-7-yl}-1H-pyrimidine-2,4-dione | 913972-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-{(1R,5R,7R,8S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-8-hydroxy-6-oxa-bicyclo[3.2.1]oct-3-en-7-yl}-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(1R,5R,7R,8S)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-8-hydroxy-6-oxabicyclo[3.2.1]oct-3-en-7-yl]pyrimidine-2,4-dione
• CAS: 913972-70-0
• 化学式: C₃₃H₃₂N₂O₇
• 分子量: 568.626
• InChiKey: AAMSPKSRCCBBLG-ODOXFGBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-{(1R,5R,7R,8S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-8-hydroxy-6-oxa-bicyclo[3.2.1]oct-3-en-7-yl}-1H-pyrimidine-2,4-dione 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到(1R,5R,6R,8S)-8-(2-cyanoethoxy(diisopropylamino)phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-6-(uracil-1-yl)-7-oxabicyclo[3.2.1]oct-2-ene
  参考文献：
  名称：

  Two Carbocyclic Locked Nucleic Acid Analogues Give Structural Information about the Role of Hydration in A-Type Duplexes

  摘要：

  Two locked nucleic acid (LNA) analogues with three-carbon 24 linkages, saturated or unsaturated, are synthesized using a ring-closing metathesis based strategy. Strongly stabilized duplexes with complementary RNA and slightly destabilized duplexes with complementary DNA are observed. CD-spectroscopy indicates a less pronounced shift toward A-type duplexes compared to LNA. These results combining a strong N-type conformation with the absence of a 2'-oxygen demonstrate a stronger importance of minor groove hydration in an intermediate duplex type than in an A-type duplex.

  DOI：

  10.1080/15257770701544377
• 作为产物：
  描述：

  2'-deoxy-2'-C-allyl-3',5'-di-O-(tert-butyldimethylsilyl)-4'-C-vinyluridine 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 53.0h， 生成 1-{(1R,5R,7R,8S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-8-hydroxy-6-oxa-bicyclo[3.2.1]oct-3-en-7-yl}-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Analogues of a Locked Nucleic Acid with Three-Carbon 2‘,4‘-Linkages:  Synthesis by Ring-Closing Metathesis and Influence on Nucleic Acid Duplex Stability and Structure

  摘要：

  Two bicyclic 2'-deoxynucleoside analogues containing a saturated and an unsaturated three-carbon 2', 4'-linkage, respectively, have been synthesized using a ring-closing metathesis-based linear strategy starting from uridine. Both analogues have been incorporated into oligodeoxynucleotide sequences and increased the stability of DNA:RNA hybrid duplexes (Delta T-m similar to 2.5-5.0 degrees C per modification) and decreased the stability of dsDNA duplexes (Delta T-m similar to 2.5-1.0 degrees C per modification). CD spectroscopy revealed that the bicyclic nucleosides induced formation of A-type-like duplexes albeit to a lesser degree than found for locked nucleic acid (LNA) monomers. From the CD data and UV melting analysis, we propose that the 2'-oxygen atom of the bicyclic moiety is essential for the formation of stabilized A-type-like dsDNA but not for the formation of a stabilized A-type DNA:RNA hybrid.

  DOI：

  10.1021/jo061225g

文献信息

• Two Carbocyclic Locked Nucleic Acid Analogues Give Structural Information about the Role of Hydration in A-Type Duplexes
  作者：Nanna Albæk、Michael Petersen、Poul Nielsen

  DOI：10.1080/15257770701544377

  日期：2007.11.26

  Two locked nucleic acid (LNA) analogues with three-carbon 24 linkages, saturated or unsaturated, are synthesized using a ring-closing metathesis based strategy. Strongly stabilized duplexes with complementary RNA and slightly destabilized duplexes with complementary DNA are observed. CD-spectroscopy indicates a less pronounced shift toward A-type duplexes compared to LNA. These results combining a strong N-type conformation with the absence of a 2'-oxygen demonstrate a stronger importance of minor groove hydration in an intermediate duplex type than in an A-type duplex.
• Analogues of a Locked Nucleic Acid with Three-Carbon 2‘,4‘-Linkages:  Synthesis by Ring-Closing Metathesis and Influence on Nucleic Acid Duplex Stability and Structure
  作者：Nanna Albæk,、Michael Petersen、Poul Nielsen

  DOI：10.1021/jo061225g

  日期：2006.9.1

  Two bicyclic 2'-deoxynucleoside analogues containing a saturated and an unsaturated three-carbon 2', 4'-linkage, respectively, have been synthesized using a ring-closing metathesis-based linear strategy starting from uridine. Both analogues have been incorporated into oligodeoxynucleotide sequences and increased the stability of DNA:RNA hybrid duplexes (Delta T-m similar to 2.5-5.0 degrees C per modification) and decreased the stability of dsDNA duplexes (Delta T-m similar to 2.5-1.0 degrees C per modification). CD spectroscopy revealed that the bicyclic nucleosides induced formation of A-type-like duplexes albeit to a lesser degree than found for locked nucleic acid (LNA) monomers. From the CD data and UV melting analysis, we propose that the 2'-oxygen atom of the bicyclic moiety is essential for the formation of stabilized A-type-like dsDNA but not for the formation of a stabilized A-type DNA:RNA hybrid.