Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-trifluoromethyl-benzoimidazol-1-yl)-tetrahydro-furan-3-yl ester | 631899-59-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 苯并咪唑核糖核苷和核糖核苷酸
• 英文名称: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-trifluoromethyl-benzoimidazol-1-yl)-tetrahydro-furan-3-yl ester
• CAS: 631899-59-7
• 化学式: C₁₉H₁₉F₃N₂O₇
• 分子量: 444.364
• InChiKey: PZEJTCRSHRFRDU-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  105.95
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-trifluoromethyl-benzoimidazol-1-yl)-tetrahydro-furan-3-yl ester 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 以90%的产率得到1-deoxy-1-(6-(trifluoromethyl)-1H-benzimidazol-1-yl)-β-D-ribofuranose
  参考文献：
  名称：

  RNA RECOGNITION BY FLUOR-AROMATIC SUBSTITUTED

  摘要：

  RNA exhibits a higher structural diversity than DNA and is an important molecule in the biology of life. It shows a number of secondary structures such as duplexes, hairpin loops, bulges, internal loops, etc. However, in natural RNA, bases are limited to the four Predominant structures Q, C, A, and G and so the number of compounds that can be used for investigation of parameters of base stacking, base pairing, and hydrogen bond is limited. We synthesized different fluoromodifications of RNA building blocks: 1'-deoxy- 1'-phenyl-beta-D-ribofuranose (B), 1'-deoxy- 1'-(4-fluorophenyl)-beta-D-ribofuranose (4 FB), 1'-deoxy- 1'-(2,4-difluorophenyl)-beta-D-ribofuranose (2,4 DFB), 1'-deoxy-1'-(2,4,5-trifluorophenyl)-beta-D-ribofuranose (2,4,5 TFB), 1'-deoxy-1'-(2,4,6-trifluorophenyl)-beta-D-ribofuranose, 1'-deoxy- 1'-(pentafluorophenyl)-beta-D-ribofuranose (PFB), 1'-deoxy-1'-(benzimidazol-1-yl)-beta-D-ribofuranose (BI), 1'-deoxy-1'-(4-fluoro- 1H-benzimidazol-1-yl)-beta-D-ribofuranose (4 FBI), 1'-deoxy-1'-(6-fluoro-1H-benzimidazol-1-y1)-beta-D-ribofuranose(6FBI), 1'-deoxy-1'-(4,6-difluoro-IH-benzimidazol-1-yl)-beta-D-ribofuranose(4,6 DFBI), 1'-deoxy-1'-(4-trifluoromethyl-1H-benzimidazol-1-yl)-beta-D-ribofuranose (4 TFM), 1'-deoxy-1'-(5-trifluoromethyl-1H-benzimidazol-1-yl)-beta-D-ribofuranose (5 TFM), and 1'-deoxy-1'-(6-trifluoromethyl- 1H-benzimidazol-1-yl)-beta-D-ribofuranose (6 TFM). These amidites were incorporated and tested in a defined A, U-rich RNA sequence (12-mer, 5'-CUU UUC XUU CUU-3' paired with 3'-GAA AAG YAA GAA-5'). Ono one position was modified, marked as X and Y, respectively. UV melting profiles of those oligonucleotides were measured.

  DOI：

  10.1081/ncn-200059755
• 作为产物：
  描述：

  四乙酰核糖 、 5-三氟甲基-1H-苯并咪唑 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40%的产率得到Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-trifluoromethyl-benzoimidazol-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  RNA RECOGNITION BY FLUOR-AROMATIC SUBSTITUTED

  摘要：

  RNA exhibits a higher structural diversity than DNA and is an important molecule in the biology of life. It shows a number of secondary structures such as duplexes, hairpin loops, bulges, internal loops, etc. However, in natural RNA, bases are limited to the four Predominant structures Q, C, A, and G and so the number of compounds that can be used for investigation of parameters of base stacking, base pairing, and hydrogen bond is limited. We synthesized different fluoromodifications of RNA building blocks: 1'-deoxy- 1'-phenyl-beta-D-ribofuranose (B), 1'-deoxy- 1'-(4-fluorophenyl)-beta-D-ribofuranose (4 FB), 1'-deoxy- 1'-(2,4-difluorophenyl)-beta-D-ribofuranose (2,4 DFB), 1'-deoxy-1'-(2,4,5-trifluorophenyl)-beta-D-ribofuranose (2,4,5 TFB), 1'-deoxy-1'-(2,4,6-trifluorophenyl)-beta-D-ribofuranose, 1'-deoxy- 1'-(pentafluorophenyl)-beta-D-ribofuranose (PFB), 1'-deoxy-1'-(benzimidazol-1-yl)-beta-D-ribofuranose (BI), 1'-deoxy-1'-(4-fluoro- 1H-benzimidazol-1-yl)-beta-D-ribofuranose (4 FBI), 1'-deoxy-1'-(6-fluoro-1H-benzimidazol-1-y1)-beta-D-ribofuranose(6FBI), 1'-deoxy-1'-(4,6-difluoro-IH-benzimidazol-1-yl)-beta-D-ribofuranose(4,6 DFBI), 1'-deoxy-1'-(4-trifluoromethyl-1H-benzimidazol-1-yl)-beta-D-ribofuranose (4 TFM), 1'-deoxy-1'-(5-trifluoromethyl-1H-benzimidazol-1-yl)-beta-D-ribofuranose (5 TFM), and 1'-deoxy-1'-(6-trifluoromethyl- 1H-benzimidazol-1-yl)-beta-D-ribofuranose (6 TFM). These amidites were incorporated and tested in a defined A, U-rich RNA sequence (12-mer, 5'-CUU UUC XUU CUU-3' paired with 3'-GAA AAG YAA GAA-5'). Ono one position was modified, marked as X and Y, respectively. UV melting profiles of those oligonucleotides were measured.

  DOI：

  10.1081/ncn-200059755

文献信息

• Synthesis of Modified RNA-Oligonucleotides for Structural Investigations
  作者：A. [Zbreve]ivković、J. W. Engels

  DOI：10.1081/ncn-120022827

  日期：2003.10

  incorporated and tested in a defined A, U- rich RNA sequence (12-mer, 5′-CUU UUC XUU CUU-3′ paired with 3′-GAA AAG YAA GAA-5’) (Schweitzer, B.A.; Kool, E.T. Aromatic nonpolar nucleosides as hydrophobic isosters of pyrimidine and purine nucleosides. J. Org. Chem. 1994, 59, 7238 pp.). Only one position was modified, marked as X and Y respectively. UV melting profiles of those oligonucleotides were measured

  摘要RNA具有比DNA更高的结构多样性，是生命生物学中的重要分子。它显示了许多二级结构，例如双链体，发夹环，凸起，内部环等。但是，在天然RNA中，碱基仅限于四个主要结构U，C，A和G，因此可以用于研究碱基堆积，碱基配对和氢键的参数是有限的。我们合成了不同的RNA修饰基团氟修饰：1'-deoxy-1'-（2,4,6-trifluorophenyl）-ß-D-ribfuranose（F），1'-deoxy-1'-（2,4,5 -三氟苯基）-β-D-呋喃核糖（M）和1'-脱氧-1'-（5-三氟甲基-1H-苯并咪唑-1-基）-β-D-核呋喃糖（D）。那些亚酰胺掺入并在确定的富含U，U的RNA序列（12-mer，5'-CUU UUC XUU CUU-3'与3'-GAA AAG YAA GAA-5'配对（Schweitzer，BA; Kool，ET）芳香非极性核苷作为嘧啶和嘌呤核苷的疏水等位异构体。J