3-nitro-4-[(5'-O-4,4-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl | 936739-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-nitro-4-[(5'-O-4,4-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl
• 英文别名: (2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(2-nitro-4-phenylphenyl)oxolan-3-ol
• CAS: 936739-71-8
• 化学式: C₃₈H₃₅NO₇
• 分子量: 617.698
• InChiKey: VYFYCYYFYNCKLT-HKIDPNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-nitro-4-[(5'-O-4,4-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到3-nitro-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-3'-(N,N-diisopropylamino-2-cyanoethyl-phosphino)-2'-deoxy-β-D-ribofuranosyl]biphenyl
  参考文献：
  名称：

  A fluorescence-quencher pair for DNA hybridization studies based on hydrophobic base surrogates

  摘要：

  The synthesis of the novel, fluorescent 3-aminobiphenyl-C-nucleoside M as well as the corresponding building block for oligodeoxynucleotide synthesis is described. M was incorporated into oligodeoxynucleotides via standard phosphoramidite chemistry and the thermal stabilities of duplexes with one and three consecutive M-M, M-P, and M-O pairs, where P denotes an unmodified biphenyl C-nucleoside and O a 3,5-dinitrobiphenyl-C-nucleoside, were determined. It was found that duplexes containing three consecutive M-O pairs were the most stable in the series, notably more stable than a duplex with one additional natural G-C pair instead of the modified residues. Furthermore it was found that the fluorescence of M is efficiently quenched in a duplex when placed opposite to the dinitrophenyl unit O. Thus M and O constitute a novel fluorophore/quencher pair that is orthogonal to natural base pairs in its recognition properties enabling its use as highly specific tags with reporting properties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.095
• 作为产物：
  描述：

  3-nitro-4-(2'-deoxy-3',5'-O-tetraisopropyl-oxydisilyl-D-ribofuranosyl)biphenyl 在 吡啶 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 20.5h， 生成 3-nitro-4-[(5'-O-4,4-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl
  参考文献：
  名称：

  A fluorescence-quencher pair for DNA hybridization studies based on hydrophobic base surrogates

  摘要：

  The synthesis of the novel, fluorescent 3-aminobiphenyl-C-nucleoside M as well as the corresponding building block for oligodeoxynucleotide synthesis is described. M was incorporated into oligodeoxynucleotides via standard phosphoramidite chemistry and the thermal stabilities of duplexes with one and three consecutive M-M, M-P, and M-O pairs, where P denotes an unmodified biphenyl C-nucleoside and O a 3,5-dinitrobiphenyl-C-nucleoside, were determined. It was found that duplexes containing three consecutive M-O pairs were the most stable in the series, notably more stable than a duplex with one additional natural G-C pair instead of the modified residues. Furthermore it was found that the fluorescence of M is efficiently quenched in a duplex when placed opposite to the dinitrophenyl unit O. Thus M and O constitute a novel fluorophore/quencher pair that is orthogonal to natural base pairs in its recognition properties enabling its use as highly specific tags with reporting properties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.095