(2R,3S,5R)-5-(2,3-Difluoro-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol | 705281-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,5R)-5-(2,3-Difluoro-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol
• 英文别名: (2R,3S,5R)-5-(2,3-difluorophenyl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 705281-32-9
• 化学式: C₁₁H₁₂F₂O₃
• 分子量: 230.211
• InChiKey: BNXDTOIIFGRPMB-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-(2,3-Difluoro-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,3-difluoro-phenyl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Efforts To Expand the Genetic Alphabet:  Identification of a Replicable Unnatural DNA Self-Pair

  摘要：

  Six unnatural nucleotides featuring fluorine-substituted phenyl nucleobase analogues have been synthesized, incorporated into DNA, and characterized in terms of the structure and replication properties of the self-pairs they form. Each unnatural self-pair is accommodated in B-form DNA without detectable structural perturbation, and all are thermally stable and selective to roughly the same degree. Furthermore, the efficiency of polymerase-mediated mispair synthesis is similar for each unnatural nucleotide in the template. In contrast, the efficiency of polymerase-mediated self-pair extension is highly dependent on the specific fluorine substitution pattern. The most promising unnatural base pair candidate of this series is the 3-fluorobenzene self-pair, which is replicated with reasonable efficiency and selectivity.

  DOI：

  10.1021/ja049961u
• 作为产物：
  描述：

  2,3-二氟溴苯 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.42h， 生成 (2R,3S,5R)-5-(2,3-Difluoro-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Efforts To Expand the Genetic Alphabet:  Identification of a Replicable Unnatural DNA Self-Pair

  摘要：

  Six unnatural nucleotides featuring fluorine-substituted phenyl nucleobase analogues have been synthesized, incorporated into DNA, and characterized in terms of the structure and replication properties of the self-pairs they form. Each unnatural self-pair is accommodated in B-form DNA without detectable structural perturbation, and all are thermally stable and selective to roughly the same degree. Furthermore, the efficiency of polymerase-mediated mispair synthesis is similar for each unnatural nucleotide in the template. In contrast, the efficiency of polymerase-mediated self-pair extension is highly dependent on the specific fluorine substitution pattern. The most promising unnatural base pair candidate of this series is the 3-fluorobenzene self-pair, which is replicated with reasonable efficiency and selectivity.

  DOI：

  10.1021/ja049961u

文献信息

• Efforts To Expand the Genetic Alphabet:  Identification of a Replicable Unnatural DNA Self-Pair
  作者：Allison A. Henry、Anne Goldbech Olsen、Shigeo Matsuda、Chengzhi Yu、Bernhard H. Geierstanger、Floyd E. Romesberg

  DOI：10.1021/ja049961u

  日期：2004.6.1

  Six unnatural nucleotides featuring fluorine-substituted phenyl nucleobase analogues have been synthesized, incorporated into DNA, and characterized in terms of the structure and replication properties of the self-pairs they form. Each unnatural self-pair is accommodated in B-form DNA without detectable structural perturbation, and all are thermally stable and selective to roughly the same degree. Furthermore, the efficiency of polymerase-mediated mispair synthesis is similar for each unnatural nucleotide in the template. In contrast, the efficiency of polymerase-mediated self-pair extension is highly dependent on the specific fluorine substitution pattern. The most promising unnatural base pair candidate of this series is the 3-fluorobenzene self-pair, which is replicated with reasonable efficiency and selectivity.