(1S,6R,8R)-8-(3N-benzylthymin-1-yl)-6-hydroxy-1-hydroxymethyl-3,9-dioxabicyclo[4.3.0]nonane | 1112393-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (1S,6R,8R)-8-(3N-benzylthymin-1-yl)-6-hydroxy-1-hydroxymethyl-3,9-dioxabicyclo[4.3.0]nonane
• CAS: 1112393-87-9
• 化学式: C₂₀H₂₄N₂O₆
• 分子量: 388.42
• InChiKey: JPLUTYUHUYHNOD-AHRSYUTCSA-N

物化性质

• 沸点：
  600.8±65.0 °C(predicted)
• 密度：
  1.424±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  (1R,6R,8R)-6-benzyloxy-8-(3N-benzylthymin-1-yl)-1-(4,4'-dimethoxytrityloxymethyl)-3,9-dioxabicyclo[4.3.0]nonane 在 palladium(II) hydroxide/carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以100%的产率得到(1S,6R,8R)-8-(3N-benzylthymin-1-yl)-6-hydroxy-1-hydroxymethyl-3,9-dioxabicyclo[4.3.0]nonane
  参考文献：
  名称：

  Synthesis of Bicyclic 2′-Deoxynucleosides with α-l-ribo- and β-d-xylo-Configurations and Restricted S- and N-Type Conformations

  摘要：

  Two bicyclic 2'-deoxynucleoside analogues are synthesized in 12 steps each from thymidine. With a six-membered ring fused to the C3'-C4' bond and an alpha-L-ribo- and a beta-D-xylo-configuration, these are con formationally restricted in an S- and an N-type conformation, respectively. The constitutions were proven by X-ray crystallography. ne beta-D-xylo-configured analogue is successfully converted to a 3'-phosphoramidite and incorporated into oligodeoxynucleotides, which are found to hybridize to DNA and RNA complements with decreased affinity.

  DOI：

  10.1021/jo8023472