1-(3-C-allyl-2-O-methyl-β-D-ribo-pentofuranosyl)thymine | 250689-63-5

• 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: 1-(3-C-allyl-2-O-methyl-β-D-ribo-pentofuranosyl)thymine
• 英文别名: 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-4-prop-2-enyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 250689-63-5
• 化学式: C₁₄H₂₀N₂O₆
• 分子量: 312.323
• InChiKey: ZRDDCETVHIFZQN-IQOUGMIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  1-(3-C-allyl-2-O-methyl-β-D-ribo-pentofuranosyl)thymine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 1-[3-C-allyl-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-pentofuranosyl]thymine
  参考文献：
  名称：

  Evaluation of Oligonucleotides Containing Two Novel 2′-O-Methyl Modified Nucleotide Monomers: A 3′-C-Allyl and a 2′-O-3′-C-Linked Bicyclic Derivative

  摘要：

  The two ribo-configured nucleosides 1-(3-C-allyl-2-O-methyl-beta-D-ribo-pentofuranosyl)thymine 3 and (1S,5R,6R,8R)-5-hydroxy-6-(hydroxymethyl)-1-methoxy-8-(thymin-1-yl )- 2,7-dioxabicyclo[3.3.0]octane 6 have been transformed into their corresponding phosphoramidites, 5 and 8 respectively, and used as building blocks for the synthesis of modified oligonucleotides. The oligonucleotides were shown to hybridize with decreased binding affinity towards complementary single stranded DNA and RNA.

  DOI：

  10.1080/07328319908044861
• 作为产物：
  描述：

  1-(3-C-allyl-3,5-di-O-benzyl-2-O-methyl-β-D-ribo-pentofuranosyl)thymine 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到1-(3-C-allyl-2-O-methyl-β-D-ribo-pentofuranosyl)thymine
  参考文献：
  名称：

  Evaluation of Oligonucleotides Containing Two Novel 2′-O-Methyl Modified Nucleotide Monomers: A 3′-C-Allyl and a 2′-O-3′-C-Linked Bicyclic Derivative

  摘要：

  The two ribo-configured nucleosides 1-(3-C-allyl-2-O-methyl-beta-D-ribo-pentofuranosyl)thymine 3 and (1S,5R,6R,8R)-5-hydroxy-6-(hydroxymethyl)-1-methoxy-8-(thymin-1-yl )- 2,7-dioxabicyclo[3.3.0]octane 6 have been transformed into their corresponding phosphoramidites, 5 and 8 respectively, and used as building blocks for the synthesis of modified oligonucleotides. The oligonucleotides were shown to hybridize with decreased binding affinity towards complementary single stranded DNA and RNA.

  DOI：

  10.1080/07328319908044861