(5S,6S)-5-Methyl-2'-deoxycytidine glycol | 176021-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,6S)-5-Methyl-2'-deoxycytidine glycol
• 英文别名: (4S,5S)-6-amino-4,5-dihydroxy-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-4H-pyrimidin-2-one
• CAS: 176021-89-9
• 化学式: C₁₀H₁₇N₃O₆
• 分子量: 275.261
• InChiKey: CARMKKLLEVUJIC-LFOMBHIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-Methyl-2'-deoxycytidine glycol 反应 125.0h， 生成 (-)-cis-(5R,6S)-5,6-dihydroxy-5,6-dihydrothymidine
  参考文献：
  名称：

  Synthesis and Kinetic Study of the Deamination of the Cis Diastereomers of 5,6-Dihydroxy-5,6-dihydro-5-methyl-2‘-deoxycytidine

  摘要：

  The main objectives of the present work were the synthesis of the two cis diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine and the kinetic study of their hydrolytic deamination. The preparation of the two glycols, two main (OH)-O-.-mediated oxidation products of 5-methyl-2'-deoxycytidine, was achieved in two steps. The first one involved the synthesis of the two trans-(5R,6S)- and (5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine. In a subsequent step, the bromohydrins were specifically converted into the cis-(5S,6S) and (5R,6R) diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine, respectively, under slightly alkaline conditions. The resulting glycols were purified by reverse phase high performance liquid chromatography and characterized by extensive spectroscopy measurements including C-13- and H-1-NMR analyses. Exact mass determination was Inferred from high resolution fast atom bombardment mass spectrometry measurements. Circular dichroism spectroscopy confirmed the diastereomeric relationship existing between the pair of glycols. Kinetic study of the deamination of the above glycols was carried out in phosphate buffer solutions (pH 7) at two different temperatures (37 degrees C and 25 degrees C) in order to determine the thermodynamic and kinetic parameters of the reaction.

  DOI：

  10.1021/jo951900e
• 作为产物：
  描述：

  5-甲基-2'-脱氧胞苷 在 溴 、 sodium acetate 、 碳酸氢铵 作用下， 反应 5.25h， 生成 (5S,6S)-5-Methyl-2'-deoxycytidine glycol
  参考文献：
  名称：

  Synthesis and Kinetic Study of the Deamination of the Cis Diastereomers of 5,6-Dihydroxy-5,6-dihydro-5-methyl-2‘-deoxycytidine

  摘要：

  The main objectives of the present work were the synthesis of the two cis diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine and the kinetic study of their hydrolytic deamination. The preparation of the two glycols, two main (OH)-O-.-mediated oxidation products of 5-methyl-2'-deoxycytidine, was achieved in two steps. The first one involved the synthesis of the two trans-(5R,6S)- and (5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine. In a subsequent step, the bromohydrins were specifically converted into the cis-(5S,6S) and (5R,6R) diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine, respectively, under slightly alkaline conditions. The resulting glycols were purified by reverse phase high performance liquid chromatography and characterized by extensive spectroscopy measurements including C-13- and H-1-NMR analyses. Exact mass determination was Inferred from high resolution fast atom bombardment mass spectrometry measurements. Circular dichroism spectroscopy confirmed the diastereomeric relationship existing between the pair of glycols. Kinetic study of the deamination of the above glycols was carried out in phosphate buffer solutions (pH 7) at two different temperatures (37 degrees C and 25 degrees C) in order to determine the thermodynamic and kinetic parameters of the reaction.

  DOI：

  10.1021/jo951900e

文献信息

• Synthesis and Kinetic Study of the Deamination of the <i>Cis</i> Diastereomers of 5,6-Dihydroxy-5,6-dihydro-5-methyl-2‘-deoxycytidine
  作者：Carine Bienvenu、Jean Cadet

  DOI：10.1021/jo951900e

  日期：1996.1.1

  The main objectives of the present work were the synthesis of the two cis diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine and the kinetic study of their hydrolytic deamination. The preparation of the two glycols, two main (OH)-O-.-mediated oxidation products of 5-methyl-2'-deoxycytidine, was achieved in two steps. The first one involved the synthesis of the two trans-(5R,6S)- and (5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine. In a subsequent step, the bromohydrins were specifically converted into the cis-(5S,6S) and (5R,6R) diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine, respectively, under slightly alkaline conditions. The resulting glycols were purified by reverse phase high performance liquid chromatography and characterized by extensive spectroscopy measurements including C-13- and H-1-NMR analyses. Exact mass determination was Inferred from high resolution fast atom bombardment mass spectrometry measurements. Circular dichroism spectroscopy confirmed the diastereomeric relationship existing between the pair of glycols. Kinetic study of the deamination of the above glycols was carried out in phosphate buffer solutions (pH 7) at two different temperatures (37 degrees C and 25 degrees C) in order to determine the thermodynamic and kinetic parameters of the reaction.