(1R,6R,8R)-6-benzyloxy-8-(3N-benzylthymin-1-yl)-1-(4,4'-dimethoxytrityloxymethyl)-3,9-dioxabicyclo[4.3.0]nonane | 1112393-84-6

• 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: (1R,6R,8R)-6-benzyloxy-8-(3N-benzylthymin-1-yl)-1-(4,4'-dimethoxytrityloxymethyl)-3,9-dioxabicyclo[4.3.0]nonane
• CAS: 1112393-84-6
• 化学式: C₄₈H₄₈N₂O₈
• 分子量: 780.918
• InChiKey: PBQJDDYYUVTODE-ICMRLIHDSA-N

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1N-[3'-O-benzyl-5'-O-(4,4-dimethoxytrityl)-3'-C-(2-hydroxyethyl)-4'-C-methanesulfonyloxymethyl-2'-deoxy-β-D-xylofuranosyl]-3N-benzylthymine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 oil 为溶剂， 以58%的产率得到(1R,6R,8R)-6-benzyloxy-8-(3N-benzylthymin-1-yl)-1-(4,4'-dimethoxytrityloxymethyl)-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