1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-vinyltetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione | 1052725-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-vinyltetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-[(2R,3R,4S,5R)-5-ethenyl-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1052725-26-4
• 化学式: C₂₆H₂₈N₂O₆
• 分子量: 464.518
• InChiKey: OFKCPPAMYSJZKU-MWXBQQNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-vinyltetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 camphor-10-sulfonic acid 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以21%的产率得到(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis of 6′-Branched Locked Nucleic Acid by a Radical TEMPO-Scavanged Stereoselective Mercury Cyclization

  摘要：

  A 6'(R)-hydroxymethyl derivative of the locked nucleic acid (LNA)-thymidine monomer has been synthesized by a stereoselective mercury cyclization and subsequent use of TEMPO as a radical scavenger. This Compound was converted to an azide derivative, which in a Huisgen-type [3 + 2] cycloaddition afforded a double-headed nucleoside with a triazole linking an additional thymine to the 6'-position of the LNA-nucleoside monomer.

  DOI：

  10.1021/jo801081t
• 作为产物：
  描述：

  1-(2-O-acetyl-3,5-di-O-benzyl-4-C-vinyl-β-D-ribofuranosyl)thymine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以85 %的产率得到1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-vinyltetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  7'-取代的 2'-O-4'-C-亚乙基桥核酸 (ENA)-胸苷单体的合成

  摘要：

  在 7' 位带有烷基取代基的新型 2'- O -4' - C - 乙烯桥核酸 (ENA) 单体，分别为 7'-( S )-Me-ENA 和 7'-( S )-合成了Et-ENA。双环结构的构建得益于关键的闭环复分解步骤和随后的环状烯醇醚部分的立体选择性还原。

  DOI：

  10.1002/ejoc.202300946

文献信息

• [EN] 7'-SUBSTITUTED 2'-O-4'-C-ETHYLENE-BRIDGED NUCLEIC ACID (ENA) MONOMERS AND USES THEREOF<br/>[FR] MONOMÈRES D'ACIDES NUCLÉIQUES À PONT 2'-O-4'-C-ÉTHYLÈNE SUBSTITUÉS EN 7' ET LEURS UTILISATIONS
  申请人：JANSSEN SCIENCES IRELAND UNLIMITED CO

  公开号：WO2022043531A1

  公开（公告）日：2022-03-03

  The present disclosure relates to ethylene-bridged nucleic acid (ENA) compounds, which may find use in therapy and/or prophylaxis. These ENA compounds may also find use as building blocks for preparing oligonucleotides, said oligonucleotides also finding use in therapy and/or prophylaxis. These compounds may be mono- or oligonucleotide derivatives comprising at least one of the following fragment: Formula (IV), wherein R1 is an optionally substituted C1-C6 alkyl moiety.

  本公开涉及乙烯桥联核酸（ENA）化合物，可以用于治疗和/或预防。这些ENA化合物也可以用作制备寡核苷酸的构建块，所述寡核苷酸也可以用于治疗和/或预防。这些化合物可以是单核苷酸或寡核苷酸衍生物，包括以下至少一种片段：公式（IV），其中R1是一个可选的取代的C1-C6烷基基团。
• Synthesis of 6′-Branched Locked Nucleic Acid by a Radical TEMPO-Scavanged Stereoselective Mercury Cyclization
  作者：Gerald Enderlin、Poul Nielsen

  DOI：10.1021/jo801081t

  日期：2008.9.1

  A 6'(R)-hydroxymethyl derivative of the locked nucleic acid (LNA)-thymidine monomer has been synthesized by a stereoselective mercury cyclization and subsequent use of TEMPO as a radical scavenger. This Compound was converted to an azide derivative, which in a Huisgen-type [3 + 2] cycloaddition afforded a double-headed nucleoside with a triazole linking an additional thymine to the 6'-position of the LNA-nucleoside monomer.
• Synthesis of 7’‐Substituted 2’‐<i>O</i>‐4’‐<i>C</i>‐Ethylene Bridged Nucleic Acid (ENA)‐Thymidine Monomers
  作者：Prabhakar Sunchu、Sandrine Gaurrand、Émilie Lambert、Jérôme Guillemont、Leonid Beigelman、Julien Brioche、Serge R. Piettre

  DOI：10.1002/ejoc.202300946

  日期：2024.1.2

  Novel 2’-O-4’-C-Ethylene-bridged Nucleic Acid (ENA) monomers bearing an alkyl substituent at the 7’-position, respectively 7’-(S)-Me-ENA and 7’-(S)-Et-ENA, were synthesized. The bicyclic structures were built thank to a key ring-closing metathesis step and a subsequent stereoselective reduction of the cyclic enol ether moiety.

  在 7' 位带有烷基取代基的新型 2'- O -4' - C - 乙烯桥核酸 (ENA) 单体，分别为 7'-( S )-Me-ENA 和 7'-( S )-合成了Et-ENA。双环结构的构建得益于关键的闭环复分解步骤和随后的环状烯醇醚部分的立体选择性还原。