1N-[3'-C-(2-chloroethyl)-4'-C-hydroxymethyl-2'-deoxy-β-D-xylofuranosyl]thymine | 1112393-66-4

• 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: 1N-[3'-C-(2-chloroethyl)-4'-C-hydroxymethyl-2'-deoxy-β-D-xylofuranosyl]thymine
• 英文别名: 1-[(2R,4S)-4-(2-chloroethyl)-4-hydroxy-5,5-bis(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1112393-66-4
• 化学式: C₁₃H₁₉ClN₂O₆
• 分子量: 334.757
• InChiKey: RQDIEEIVTQNQMW-BXKDBHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1S,6R,8R)-6-benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane 在 三氯化硼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以50%的产率得到1N-[3'-C-(2-chloroethyl)-4'-C-hydroxymethyl-2'-deoxy-β-D-xylofuranosyl]thymine
  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