1N-(3'-C-allyl-3'-O-benzyl-4'-C-hydroxymethyl-5'-O-methanesulfonyl-2'-deoxy-β-D-xylofuranosyl)thymine | 1112393-38-0

• 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-5'-O-methanesulfonyl-2'-deoxy-β-D-xylofuranosyl)thymine
• 英文别名: [(2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-phenylmethoxy-3-prop-2-enyloxolan-2-yl]methyl methanesulfonate
• CAS: 1112393-38-0
• 化学式: C₂₂H₂₈N₂O₈S
• 分子量: 480.539
• InChiKey: DSLRRHSBGHFGRS-STZQEDGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1N-(3'-C-allyl-3'-O-benzyl-4'-C-hydroxymethyl-5'-O-methanesulfonyl-2'-deoxy-β-D-xylofuranosyl)thymine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 24.0h， 以75%的产率得到1N-[3'C-allyl-3'-O-benzyl-4'-C-(4,4'-dimethoxytrityloxymethyl)-5'-O-methanesulfonyl-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：

  1N-(3'-C-allyl-3'-O-benzyl-4'-C-methanesulfonyoxymethyl-5'-O-methanesulfonyl-2'-deoxy-β-D-xylofuranosyl)thymine 在 18-冠醚-6 、 水 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 96.0h， 以25%的产率得到1N-(3'-C-allyl-3'-O-benzyl-4'-C-hydroxymethyl-5'-O-methanesulfonyl-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.