2-[2-O-acetyl-3,5-di-O-benzyl-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranosyl]-1-isoquinolone | 600707-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-O-acetyl-3,5-di-O-benzyl-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranosyl]-1-isoquinolone
• 英文别名: [(2R,3R,4S,5S)-5-[(4-methylphenyl)sulfonyloxymethyl]-2-(1-oxoisoquinolin-2-yl)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl] acetate
• CAS: 600707-55-9
• 化学式: C₃₈H₃₇NO₉S
• 分子量: 683.779
• InChiKey: UBABFFCCGFQPHH-SVFYAPPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[2-O-acetyl-3,5-di-O-benzyl-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranosyl]-1-isoquinolone 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以95%的产率得到2-(3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)-1-isoquinolone
  参考文献：
  名称：

  Selective recognition of CG interruption by 2′,4′-BNA having 1-isoquinolone as a nucleobase in a pyrimidine motif triplex formation

  摘要：

  To develop a novel nucleoside analogue for the effective recognition of CG interruption in a homopurine-homopyrimidine tract of double-stranded DNA (dsDNA), we succeeded in the synthesis of a triplex-forming oligonucleotide (TFO) containing a novel 2',4'-BNA (Q(B)) bearing 1-isoquinolone as a nucleobase, and the triplex-forming ability and sequence-selectivity of the TFO (TFO-Q(B)) were examined. On melting temperature (T-m) measurements, it was found that the TFO-Q(B) formed a stable triplex DNA in a highly sequence-selective manner under near physiological conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00728-2
• 作为产物：
  描述：

  1-羟基异喹啉 、 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranose 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以83%的产率得到2-[2-O-acetyl-3,5-di-O-benzyl-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranosyl]-1-isoquinolone
  参考文献：
  名称：

  Selective recognition of CG interruption by 2′,4′-BNA having 1-isoquinolone as a nucleobase in a pyrimidine motif triplex formation

  摘要：

  To develop a novel nucleoside analogue for the effective recognition of CG interruption in a homopurine-homopyrimidine tract of double-stranded DNA (dsDNA), we succeeded in the synthesis of a triplex-forming oligonucleotide (TFO) containing a novel 2',4'-BNA (Q(B)) bearing 1-isoquinolone as a nucleobase, and the triplex-forming ability and sequence-selectivity of the TFO (TFO-Q(B)) were examined. On melting temperature (T-m) measurements, it was found that the TFO-Q(B) formed a stable triplex DNA in a highly sequence-selective manner under near physiological conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00728-2