2’-deoxy-2’,2’-difluoro-4’-methoxy-1’-O-(2-nitrobenzyl)-α-L-lyxofuranose | 1412439-65-6

• 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: 2’-deoxy-2’,2’-difluoro-4’-methoxy-1’-O-(2-nitrobenzyl)-α-L-lyxofuranose
• 英文别名: (2S,3R,5S)-4,4-difluoro-2-(hydroxymethyl)-2-methoxy-5-[(2-nitrophenyl)methoxy]oxolan-3-ol
• CAS: 1412439-65-6
• 化学式: C₁₃H₁₅F₂NO₇
• 分子量: 335.261
• InChiKey: IXRMZNMJXUKCSU-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2’-deoxy-2’,2’-difluoro-4’-methoxy-1’-O-(2-nitrobenzyl)-α-L-lyxofuranose 、 4,4'-双甲氧基三苯甲基氯 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以62%的产率得到2’-deoxy-2’,2’-difluoro-5’-O-(4,4’-dimethoxytrityl)-4’-methoxy-1’-O-(2-nitrobenzyl)-α-L-lyxofuranose
  参考文献：
  名称：

  Difluoro-C4′-oxidized Abasic Site for Efficient Amine Modification in Biological Systems

  摘要：

  An oligodeoxynucleotide (ODN) containing a 2',2'-difluorinated analogue of a C4'-oxidized abasic site (C4'-OAS) was designed for the amine modification of biomolecules that interact with nucleic acids. In contrast to the parent C4'-OAS, which yielded amine-modified products accompanied by DNA strand scission, the ODN containing the difluoro C4'-OAS efficiently yielded products carrying ODNs. The amine modification proceeded without additional reagents being required and might be applicable to reactions in biological systems.

  DOI：

  10.1021/ol302703m
• 作为产物：
  描述：

  2’,5’-dideoxy-3’-O-acetyl-2’,2’-difluoro-5’-iodo-1’-O-(2-nitrobenzyl)-α-D-ribofuranose 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 2’-deoxy-2’,2’-difluoro-4’-methoxy-1’-O-(2-nitrobenzyl)-α-L-lyxofuranose 、 2’-deoxy-2’,2’-difluoro-4’-methoxy-1’-O-(2-nitrobenzyl)-α-L-lyxofuranose
  参考文献：
  名称：

  Difluoro-C4′-oxidized Abasic Site for Efficient Amine Modification in Biological Systems

  摘要：

  An oligodeoxynucleotide (ODN) containing a 2',2'-difluorinated analogue of a C4'-oxidized abasic site (C4'-OAS) was designed for the amine modification of biomolecules that interact with nucleic acids. In contrast to the parent C4'-OAS, which yielded amine-modified products accompanied by DNA strand scission, the ODN containing the difluoro C4'-OAS efficiently yielded products carrying ODNs. The amine modification proceeded without additional reagents being required and might be applicable to reactions in biological systems.

  DOI：

  10.1021/ol302703m

文献信息

• Difluoro-C4′-oxidized Abasic Site for Efficient Amine Modification in Biological Systems
  作者：Bo Yang、Akiko Jinnouchi、Hiroshi Suemune、Mariko Aso

  DOI：10.1021/ol302703m

  日期：2012.12.7

  An oligodeoxynucleotide (ODN) containing a 2',2'-difluorinated analogue of a C4'-oxidized abasic site (C4'-OAS) was designed for the amine modification of biomolecules that interact with nucleic acids. In contrast to the parent C4'-OAS, which yielded amine-modified products accompanied by DNA strand scission, the ODN containing the difluoro C4'-OAS efficiently yielded products carrying ODNs. The amine modification proceeded without additional reagents being required and might be applicable to reactions in biological systems.