[(2S,3R,5R)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid methyl ester | 136369-43-2

• 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: [(2S,3R,5R)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid methyl ester
• 英文别名: methyl 2-[(2S,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetate
• CAS: 136369-43-2
• 化学式: C₁₃H₁₈N₂O₆
• 分子量: 298.296
• InChiKey: LVIPVQVVJQKLLM-OPRDCNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3R,5R)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid methyl ester 在 palladium on activated charcoal 吡啶 、 1H-1,2,4-三唑 、 4-二甲氨基吡啶 、 lithium hydroxide 、 ammonium hydroxide 、 叠氮化锂 、 氢气 、 三乙胺 、 sodium iodide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 100.0 ℃ 、100.0 kPa 条件下， 反应 70.0h， 生成 ((2S,3R,5R)-2-({[(4-Methoxy-phenyl)-diphenyl-methyl]-amino}-methyl)-5-{5-methyl-4-[1-methyl-pyrrolidin-(2E)-ylideneamino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-3-yl)-acetic acid pentafluorophenyl ester
  参考文献：
  名称：

  2′-deoxyribo-PNAs: A structurally novel class of polyamide nucleic acids with good RNA and DNA binding affinity

  摘要：

  2'-Deoxyribo polyamide nucleic acids (2'-deoxyribo-PNAs) 3 are a new class of DNA analogs with a 2',3'-dideoxyribose-polyamide backbone structure. 2'-Deoxyribo-PNAs as well as chimeric oligonucleotide analogs with a mixed DNA / 2'-deoxyribo-PNA structure bind to single stranded complementary nucleic acids with similar affinities as natural DNA. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00389-5
• 作为产物：
  描述：

  methyl 2-[(2S,3R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到[(2S,3R,5R)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid methyl ester
  参考文献：
  名称：

  2′-deoxyribo-PNAs: A structurally novel class of polyamide nucleic acids with good RNA and DNA binding affinity

  摘要：

  2'-Deoxyribo polyamide nucleic acids (2'-deoxyribo-PNAs) 3 are a new class of DNA analogs with a 2',3'-dideoxyribose-polyamide backbone structure. 2'-Deoxyribo-PNAs as well as chimeric oligonucleotide analogs with a mixed DNA / 2'-deoxyribo-PNA structure bind to single stranded complementary nucleic acids with similar affinities as natural DNA. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00389-5

文献信息

• Consecutive 5′- and 3′-amide linkages stabilise antisense oligonucleotides and elicit an efficient RNase H response
  作者：Sven Epple、Cameron Thorpe、Ysobel R. Baker、Afaf H. El-Sagheer、Tom Brown

  DOI：10.1039/d0cc00444h

  日期：——

  The combination of amide coupling with standard oligonucleotide synthesis enables assembly of reduced charge chimeric gapmer antisense oligonucleotides that trigger an efficient RNase H response while improving serum lifetime and cellular uptake.

  将酰胺偶联与标准寡核苷酸合成相结合，可以组装出降低电荷的嵌合间隙型反义寡核苷酸，这些寡核苷酸能够触发高效的核糖核酸酶H反应，同时提高血清寿命和细胞摄取率。
• Asymmetric synthesis of 3′-carbomethoxymethyl 3′-deoxythymidine via radical cyclization
  作者：Jean-Francois Lavallée、George Just

  DOI：10.1016/0040-4039(91)80808-j

  日期：1991.7

  An efficient asymmetric synthesis of 3'-C-carbomethoxymethyl- 3'-deoxythymidine 2, using a highly stereocontrolled radical cyclization from bromoacetal 7 to furanose 8, followed by a dimethylboron bromide mediated nucleoside formation, is described. A 96:4 beta-selectivity was observed for thionoester-controlled base attachment.
• 2′-deoxyribo-PNAs: A structurally novel class of polyamide nucleic acids with good RNA and DNA binding affinity
  作者：Peter von Matt、Alain De Mesmaeker、Uwe Pieles、Werner Zürcher、Karl-Heinz Altmann

  DOI：10.1016/s0040-4039(99)00389-5

  日期：1999.4

  2'-Deoxyribo polyamide nucleic acids (2'-deoxyribo-PNAs) 3 are a new class of DNA analogs with a 2',3'-dideoxyribose-polyamide backbone structure. 2'-Deoxyribo-PNAs as well as chimeric oligonucleotide analogs with a mixed DNA / 2'-deoxyribo-PNA structure bind to single stranded complementary nucleic acids with similar affinities as natural DNA. (C) 1999 Elsevier Science Ltd. All rights reserved.