1N-[3'-C-allyl-3'-O-benzyl-5'-O-(4,4-dimethoxytrityl)-4'-C-methanesulfonyloxymethyl-2'-deoxy-β-D-xylofuranosyl]-N3-benzylthymine | 1112393-79-9

• 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: 1N-[3'-C-allyl-3'-O-benzyl-5'-O-(4,4-dimethoxytrityl)-4'-C-methanesulfonyloxymethyl-2'-deoxy-β-D-xylofuranosyl]-N3-benzylthymine
• CAS: 1112393-79-9
• 化学式: C₅₀H₅₂N₂O₁₀S
• 分子量: 873.036
• InChiKey: NCOVHGLDVAFSHW-JUKCYWJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  63.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  133.52
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1N-[3'-C-allyl-3'-O-benzyl-5'-O-(4,4-dimethoxytrityl)-4'-C-methanesulfonyloxymethyl-2'-deoxy-β-D-xylofuranosyl]-N3-benzylthymine 在 sodium periodate 、 四氧化锇 、 水 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 5.0h， 生成
  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'-C-allyl-3'-O-benzyl-5'-O-(4,4-dimethoxytrityl)-4'-C-hydroxymethyl-2'-deoxy-β-D-xylofuranosyl]-3N-benzylthymine 、 甲基磺酰氯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到1N-[3'-C-allyl-3'-O-benzyl-5'-O-(4,4-dimethoxytrityl)-4'-C-methanesulfonyloxymethyl-2'-deoxy-β-D-xylofuranosyl]-N3-benzylthymine
  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