(S)-5-(4,4'-dimethoxytrityloxymethyl)-5H-furan-2-one | 252667-55-3

• 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: (S)-5-(4,4'-dimethoxytrityloxymethyl)-5H-furan-2-one
• 英文别名: (5S)-5-{[Bis(4-methoxyphenyl)(phenyl)methoxy]methyl}furan-2(5H)-one；(2S)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2H-furan-5-one
• CAS: 252667-55-3
• 化学式: C₂₆H₂₄O₅
• 分子量: 416.474
• InChiKey: SXLYCSPBTMLSKV-DEOSSOPVSA-N

物化性质

• 熔点：
  120-123 °C
• 沸点：
  582.4±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5-(4,4'-dimethoxytrityloxymethyl)-5H-furan-2-one 在 吡啶 、 4-二甲氨基吡啶 、 二苯甲酮 、 碘 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 29.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-1'-O-acetyl-D-ribose
  参考文献：
  名称：

  Synthesis and Incorporation into DNA of a Chemically Stable, Functional Abasic Site Analogue

  摘要：

  The abasic site building block 7 for DNA synthesis, containing a methylenephosphinic acid group at C3', was prepared in six steps and was incorporated into DNA via a combination of H-phosphonate and phosphoramidite chemistry. Corresponding oligodeoxynucleotides were shown to be chemically stable under basic conditions and fully functional at the respective hemiacetal center.

  DOI：

  10.1021/ol052045g
• 作为产物：
  描述：

  D-(+)-核糖酸-gamma-内酯 在 吡啶 、 氯磺酸甲酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-5-(4,4'-dimethoxytrityloxymethyl)-5H-furan-2-one
  参考文献：
  名称：

  Synthesis and Incorporation into DNA of a Chemically Stable, Functional Abasic Site Analogue

  摘要：

  The abasic site building block 7 for DNA synthesis, containing a methylenephosphinic acid group at C3', was prepared in six steps and was incorporated into DNA via a combination of H-phosphonate and phosphoramidite chemistry. Corresponding oligodeoxynucleotides were shown to be chemically stable under basic conditions and fully functional at the respective hemiacetal center.

  DOI：

  10.1021/ol052045g

文献信息

• Synthetic Studies Towards a Novel, Chemical Stable, Abasic Site Analogue of DNA
  作者：Caroline Hirtz、Christian J. Leumann

  DOI：10.1081/ncn-120022836

  日期：2003.10

  We synthesized the phosphinate 7 via photoaddition of methanol to the alpha, beta unsaturated deoxyribono lactone as the key step, followed by an Arbusov reaction for the introduction of phosphorous. Precursor 7 serves for the synthesis and incorporation into DNA of a novel chemically stable abasic site analogue that might act as an inhibitor for DNA glycosylases.