(1S,6R,8R)-6-hydroxy-1-hydroxymethyl-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane | 1112393-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (1S,6R,8R)-6-hydroxy-1-hydroxymethyl-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane
• 英文别名: 1-[(2R,3aR,7aS)-3a-hydroxy-7a-(hydroxymethyl)-3,4,5,7-tetrahydro-2H-furo[2,3-c]pyran-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1112393-06-2
• 化学式: C₁₃H₁₈N₂O₆
• 分子量: 298.296
• InChiKey: HLIWPPDYAWEGIX-WQAKAFBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (1S,6R,8R)-6-hydroxy-1-hydroxymethyl-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 0.5h， 以93%的产率得到(1R,6R,8R)-1-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-8-(thymin-1-yl)-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：

  (1R,6R,8R)-6-benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-8-(thymin-1-yl)-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 7.0h， 以86%的产率得到(1S,6R,8R)-6-hydroxy-1-hydroxymethyl-8-(thymin-1-yl)-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

文献信息

• Synthesis of Bicyclic 2′-Deoxynucleosides with α-<scp>l</scp>-<i>ribo</i>- and β-<scp>d</scp>-<i>xylo</i>-Configurations and Restricted <i>S</i>- and <i>N</i>-Type Conformations
  作者：Khalil I. Shaikh、Surender Kumar、Lene Lundhus、Andrew D. Bond、Pawan K. Sharma、Poul Nielsen

  DOI：10.1021/jo8023472

  日期：2009.2.20

  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.