5'-O-(prop-2-enyl)thymidine | 741687-37-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-(prop-2-enyl)thymidine
• 英文别名: 5'-O-allylthymidine；1-[(2R,4S,5R)-4-hydroxy-5-(prop-2-enoxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 741687-37-6
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: HVWMUSKATLZVRG-HBNTYKKESA-N

物化性质

• 熔点：
  97 °C
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-O-(prop-2-enyl)thymidine 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 Pentanedioic acid mono-[(2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester
  参考文献：
  名称：

  New Dinucleoside Analogues via Cross-Coupling Metathesis

  摘要：

  Synthesis of 3'-3', 5-5', and 3'-5' dimeric thymidine, linked by an olefinic chain between glycosidic moieties is described. Cross metathesis reaction of 3' or 5' O-allyl analogues of thymidine led to the expected 3'-3' and 5'-5' dimeric compounds, respectively. In order to obtain the 3'-5' dimer, 5'-O-allyl and 3'-O-allyl monomers were first linked by their free 3' OH and 5' OH groups through a glutaryl spacer; ring closing metathesis was then operated upon this temporary dimer, followed by glutaryl removal.

  DOI：

  10.1081/ncn-60595
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 吡啶 、 4-二甲氨基吡啶 、 四溴化碳 、 氨 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.5h， 生成 5'-O-(prop-2-enyl)thymidine
  参考文献：
  名称：

  One step selective 5′-O-allylation of thymidine using microwave or ultrasound activation

  摘要：

  An improved procedures for the synthesis of 5'-O-allylthymidine via one step selective allylation of thymidine using either ultrasound or microwave activation is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.008

文献信息

• DNA‐Templated Formation and N,O‐Transacetalization of N‐Methoxyoxazolidines
  作者：Aapo Aho、Tommi Österlund、Jani Rahkila、Pasi Virta

  DOI：10.1002/ejoc.202200583

  日期：2022.8.19

  AbstractDNA‐templated formation and N,O‐transacetalization of N‐methoxyoxazolidines have been studied. Compared to the reaction without a DNA‐catalyst, the hybridization‐driven N‐methoxyoxazolidine formation shows a marked rate acceleration, whereas the rate of corresponding N,O‐transacetalization is limited by the rate of decay to aldehyde intermediates. In both cases, the equilibrium yield increases markedly on the DNA template. Different hairpin architectures have been studied to evaluate the role and limits of the template effect. Furthermore, an attention has been paid to stereochemical integrity (R/S) of the N‐methoxyoxazolidine linkage. The N‐methoxyoxazolidine formation represents a dynamic pH‐responsive DNA‐templated ligation that occurs readily in slightly acidic conditions (pH 5).
• EP0789706A4
  申请人：——

  公开号：EP0789706A4

  公开（公告）日：1999-08-11
• SUGAR MODIFIED NUCLEOSIDES AND THEIR USE FOR SYNTHESIS OF OLIGONUCLEOTIDES
  申请人：ICN PHARMACEUTICALS

  公开号：EP0789706A1

  公开（公告）日：1997-08-20
• CHIMERIC ANTISENSE OLIGONUCLEOTIDES AND CELL TRANSFECTING FORMULATIONS THEREOF
  申请人：CHIRON CORPORATION

  公开号：EP1144609A2

  公开（公告）日：2001-10-17
• JP2003508459A
  申请人：——

  公开号：JP2003508459A

  公开（公告）日：2003-03-04