(1R,2R,4R,5S)-1-hydroxy-2-hydroxymethyl-4-(thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane | 207607-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,4R,5S)-1-hydroxy-2-hydroxymethyl-4-(thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane
• 英文别名: (1R,2R,4R,5S)-1-Hydroxy-2-hydroxymethyl-4-(thymin-1-yl)-3,6-dioxabicyclo-[3.2.0]heptane；1-[(1R,2R,4R,5S)-1-hydroxy-2-(hydroxymethyl)-3,6-dioxabicyclo[3.2.0]heptan-4-yl]-5-methylpyrimidine-2,4-dione
• CAS: 207607-02-1
• 化学式: C₁₁H₁₄N₂O₆
• 分子量: 270.242
• InChiKey: VCZGUQTUCVBQKJ-LUQPRHOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R,5S)-1-hydroxy-2-hydroxymethyl-4-(thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 43.0h， 生成 (1R,2R,4R,5S)-1-(2-cyanoethoxy(diisopropylamino)phosphinoxy)-2-(4,4'-dimethoxytrityloxymethyl)-4-(thymine-1-yl)-3,6-dioxabicyclo-[3.2.0]heptane
  参考文献：
  名称：

  Christensen, Nanna K.; Petersen, Michael; Nielsen, Poul, Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5458 - 5463

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose 在 palladium dihydroxide 吡啶 、 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 181.5h， 生成 (1R,2R,4R,5S)-1-hydroxy-2-hydroxymethyl-4-(thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane
  参考文献：
  名称：

  Christensen, Nanna K.; Petersen, Michael; Nielsen, Poul, Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5458 - 5463

  摘要：

  DOI：

文献信息

• New Ruthenium-Based Protocol for Cleavage of Terminal Olefins to Primary Alcohols:  Improved Synthesis of a Bicyclic Nucleoside
  作者：Pawan K. Sharma、Poul Nielsen

  DOI：10.1021/jo0491861

  日期：2004.8.1

  A new protocol for the oxidative cleavage of terminal alkenes to give exclusively primary alcohols in high yields is introduced. The protocol is based on RuO4-mediated dihydroxylation, NaIO4-mediated diol cleavage, and NaBH4-mediated reduction, but the introduction of a reducing step before the diol cleavage removes the formation of byproducts and improves the yield significantly. The new protocol

  引入了一种新的方案，用于将末端烯烃进行氧化裂解，从而以高收率的方式仅生成伯醇。该方案基于RuO 4介导的二羟基化，NaIO 4介导的二醇裂解和NaBH 4介导的还原，但是在二醇裂解之前引入还原步骤可消除副产物的形成并显着提高产率。已经开发了新的协议，并将其用于改进[3.2.0]双环阿拉伯糖核苷的制备，在反义和反义技术中具有重要的潜力。
• Oligonucleotide analogues
  申请人：Wengel Jesper

  公开号：US20050287566A1

  公开（公告）日：2005-12-29

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。这些核苷酸类似物，即锁定核苷酸类似物（LNAs），能够为寡核苷酸提供与互补RNA和DNA寡聚物的亲和力和特异性方面的有价值的改进。这种新型的LNA修饰的寡核苷酸以及LNA本身在广泛的诊断应用和治疗应用中非常有用。其中包括反义应用、PCR应用、链置换寡聚物、作为核酸聚合酶的底物、作为基于核苷酸的药物等。本发明还涉及这些应用。
• OLIGONUCLEOTIDE ANALOGUES
  申请人：Wengel Jesper

  公开号：US20100279895A1

  公开（公告）日：2010-11-04

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。这些核苷酸类似物，即LNAs（锁定核苷酸类似物），能够为寡核苷酸提供与互补RNA和DNA寡聚物相比亲和力和特异性的有价值的改进。这种新型的LNA修饰的寡核苷酸以及LNAs本身在广泛的诊断应用和治疗应用中都有用途。其中可以提到反义应用、PCR应用、链位移寡聚物、作为核酸聚合酶底物、作为核苷酸基药物等。本发明还涉及这些应用。
• Oligonucleotide Analogues
  申请人：WENGEL Jesper

  公开号：US20110245327A1

  公开（公告）日：2011-10-06

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs ( L ocked N ucleoside A nalogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。核苷酸类似物，即锁定核苷酸类似物（LNAs），能够为寡核苷酸提供有价值的改进，使其对互补的RNA和DNA寡聚体具有更高的亲和力和特异性。这种新型的LNA修饰的寡核苷酸以及LNAs本身在广泛的诊断应用和治疗应用中都很有用。其中包括反义应用、PCR应用、链置换寡聚体、作为核酸聚合酶的底物、作为基于核苷酸的药物等。本发明还涉及这些应用。
• Bi-cyclic nucleoside, nucleotide and oligonucleoide analogues
  申请人：Exiqon A/S

  公开号：EP1557424A1

  公开（公告）日：2005-07-27

  The present invention relates to novel bicyclic and tricyclic nucleoside analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerises, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型双环和三环核苷类似物以及包含此类元素的寡核苷酸。这种核苷酸类似物 LNA（锁定核苷酸类似物）能够在对互补 RNA 和 DNA 寡聚体的亲和性和特异性方面对寡核苷酸进行有价值的改进。新型 LNA 修饰寡核苷酸以及 LNA 本身可用于广泛的诊断和治疗应用。其中包括反义应用、PCR 应用、链置换寡聚体、核酸聚合底物、核苷酸类药物等。本发明也涉及此类应用。