5'-O-dimethoxytrityl-2'-[(dodecanoyl)amino]-2'-deoxyuridine | 1092661-31-8

• 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: 5'-O-dimethoxytrityl-2'-[(dodecanoyl)amino]-2'-deoxyuridine
• 英文别名: N-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]dodecanamide
• CAS: 1092661-31-8
• 化学式: C₄₂H₅₃N₃O₈
• 分子量: 727.898
• InChiKey: DSUNAHGWGKKKFI-YLGJETLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  53
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-dimethoxytrityl-2'-[(dodecanoyl)amino]-2'-deoxyuridine 、 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， 反应 1.0h， 以68%的产率得到5'-O-dimethoxytrityl-2'-[(dodecanoyl)amino]-2'-deoxyuridine-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  2′-Lipid-modified oligonucleotides via a ‘Staudinger–Vilarrasa’ reaction

  摘要：

  We report a new access to 2'-amido-2'-deoxyuridine via a Staudinger-Vilarrasa coupling reaction for the preparation of lipid-modified oligonucleotides. One or two lipidic moieties were inserted within the oligonucleotidic sequence (LONs) leading to a repertoire of original antagomir-like molecules targeting micro RNA (miRNA or miR). Melting temperature (Tm) experiments revealed that the stability of the duplexes depends on the lipid position and the number of lipid moieties inserted within the oligonucleotide sequence. Single lipid conjugations of positions 11 and 19 of LONs targeting miR-122 do not destabilize the duplexes. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.078
• 作为产物：
  描述：

  1-(月桂酰氧基)-2,5-吡咯烷二酮 、 2'-azido-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到5'-O-dimethoxytrityl-2'-[(dodecanoyl)amino]-2'-deoxyuridine
  参考文献：
  名称：

  2′-Lipid-modified oligonucleotides via a ‘Staudinger–Vilarrasa’ reaction

  摘要：

  We report a new access to 2'-amido-2'-deoxyuridine via a Staudinger-Vilarrasa coupling reaction for the preparation of lipid-modified oligonucleotides. One or two lipidic moieties were inserted within the oligonucleotidic sequence (LONs) leading to a repertoire of original antagomir-like molecules targeting micro RNA (miRNA or miR). Melting temperature (Tm) experiments revealed that the stability of the duplexes depends on the lipid position and the number of lipid moieties inserted within the oligonucleotide sequence. Single lipid conjugations of positions 11 and 19 of LONs targeting miR-122 do not destabilize the duplexes. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.078

文献信息

• 2′-Lipid-modified oligonucleotides via a ‘Staudinger–Vilarrasa’ reaction
  作者：Hubert Chapuis、Laurent Bui、Isabelle Bestel、Philippe Barthélémy

  DOI：10.1016/j.tetlet.2008.09.078

  日期：2008.11

  We report a new access to 2'-amido-2'-deoxyuridine via a Staudinger-Vilarrasa coupling reaction for the preparation of lipid-modified oligonucleotides. One or two lipidic moieties were inserted within the oligonucleotidic sequence (LONs) leading to a repertoire of original antagomir-like molecules targeting micro RNA (miRNA or miR). Melting temperature (Tm) experiments revealed that the stability of the duplexes depends on the lipid position and the number of lipid moieties inserted within the oligonucleotide sequence. Single lipid conjugations of positions 11 and 19 of LONs targeting miR-122 do not destabilize the duplexes. (c) 2008 Elsevier Ltd. All rights reserved.