1-(3-O-benzyl-5-O-methylsulfonyl-4-C-methylsulfonyloxymethyl-α-D-ribofuranosyl)thymine | 378792-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-O-benzyl-5-O-methylsulfonyl-4-C-methylsulfonyloxymethyl-α-D-ribofuranosyl)thymine
• CAS: 378792-35-9
• 化学式: C₂₀H₂₆N₂O₁₁S₂
• 分子量: 534.565
• InChiKey: KGOUDEBGIAOXFH-RYRKJORJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.99
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  180.29
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-(3-O-benzyl-5-O-methylsulfonyl-4-C-methylsulfonyloxymethyl-α-D-ribofuranosyl)thymine 在 吡啶 、 sodium hydroxide 、 silver nitrate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (1R,3S,4R,7S)-1-(4,4'-dimethoxytrityl)oxymethyl-7-(O-2-cyanoethyl-N,N-diisopropylphosphityl)oxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  SYNTHESIS AND EVALUATION OF α-LNA

  摘要：

  Three different synthetic routes to the alpha -configured LNA thymine monomer starting from D-allose or D-arabinose were investigated. The introduction of one or four alpha -LNA monomers into alpha -DNA had a destabilizing effect on the duplexes. However, a fully modified alpha -LNA sequence displayed strong recognition of complementary RNA, but no transition with DNA.

  DOI：

  10.1081/ncn-100002438
• 作为产物：
  描述：

  3-O-苄基-4-C-羟甲基-1,2-O-异亚丙基-ALPHA-D-呋喃核糖 在 吡啶 、 盐酸 作用下， 生成 1-(3-O-benzyl-5-O-methylsulfonyl-4-C-methylsulfonyloxymethyl-α-D-ribofuranosyl)thymine
  参考文献：
  名称：

  SYNTHESIS AND EVALUATION OF α-LNA

  摘要：

  Three different synthetic routes to the alpha -configured LNA thymine monomer starting from D-allose or D-arabinose were investigated. The introduction of one or four alpha -LNA monomers into alpha -DNA had a destabilizing effect on the duplexes. However, a fully modified alpha -LNA sequence displayed strong recognition of complementary RNA, but no transition with DNA.

  DOI：

  10.1081/ncn-100002438

文献信息

• α-LNA (Locked Nucleic Acid withα-D-Configuration): Synthesis and Selective Parallel Recognition of RNA
  作者：Poul Nielsen、Nanna K. Christensen、Jakob K. Dalskov

  DOI：10.1002/1521-3765(20020201)8:3<712::aid-chem712>3.0.co;2-0

  日期：2002.2.1

  alpha-LNA is presented as a stereoisomer of LNA (locked nucleic acid) with alpha-D-configuration. Three different approaches towards the thymine a-LNA monomer as well as the 5-methylcytosine alpha-LNA monomer are presented. Different alpha-LNA sequences have been synthesised and their hybridisation with complementary DNA and RNA has been evaluated by means of thermal stability experiments and circular dichroism spectroscopy. In a mixed pyrimidine sequence, alpha-LNA displays unprecedented parallel-stranded and selective RNA binding. Furthermore, a remarkable selectivity for hybridisation with RNA over DNA is indicated.