1N-(3'-C-allyl-3'-O-benzyl-4'-C-hydroxymethyl-2'-deoxy-β-D-xylofuranosyl)thymine | 1112393-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1N-(3'-C-allyl-3'-O-benzyl-4'-C-hydroxymethyl-2'-deoxy-β-D-xylofuranosyl)thymine
• 英文别名: 1-[(2R,4R)-5,5-bis(hydroxymethyl)-4-phenylmethoxy-4-prop-2-enyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1112393-21-1
• 化学式: C₂₁H₂₆N₂O₆
• 分子量: 402.447
• InChiKey: VODHCCBCSAVTJR-YLJYHZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1N-(3'-C-allyl-3'-O-benzyl-4'-C-hydroxymethyl-2'-deoxy-β-D-xylofuranosyl)thymine 、 对甲苯磺酰氯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以26%的产率得到1N-(3'-C-allyl-3'-O-benzyl-4'-C-hydroxymethyl-5'-O-p-toluenesulfonyl-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
• 作为产物：
  描述：

  聚合甲醛 、 在 sodium hydroxide 、 水 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 17.0h， 以2.19 g的产率得到1N-(3'-C-allyl-3'-O-benzyl-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

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.