(5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine | 175912-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine
• 英文别名: (5S,6R)-5-bromo-6-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-imino-5-methyl-1,3-diazinan-2-one
• CAS: 175912-34-2
• 化学式: C₁₀H₁₆BrN₃O₅
• 分子量: 338.158
• InChiKey: YITZCZFOSGQIGA-FZCTVIHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 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：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine 在 重氧水 作用下， 生成 (6-(18)O)-(5R,6S)-5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine
  参考文献：
  名称：

  Photo-sensitized formation of the cis-(5R, 6R) diastereomer of 5,6-dihydroxy-5,6-dihydro-5-methyl-2’-deoxycytidine

  摘要：

  5,6-二羟基-5,6-二氢-5-甲基-2’-脱氧胞苷是羟基自由基(^{•OH)形成的氧化产物。通过甲萘醌光敏化 5-甲基-2’-脱氧胞苷 (m5dCyd) 获得了相同的产物。 18O 标记实验使我们提出了 5,6-二羟基-5,6-二氢-5-甲基-2'-脱氧胞苷的光敏形成机制，涉及 m5dCyd 自由基阳离子。}

  DOI：

  10.1051/jcp/1997940300
• 作为产物：
  描述：

  5-甲基-2'-脱氧胞苷 在 溴 、 sodium acetate 作用下， 反应 0.5h， 以64%的产率得到(5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine
  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.
• Photo-sensitized formation of the cis-(5R, 6R) diastereomer of 5,6-dihydroxy-5,6-dihydro-5-methyl-2’-deoxycytidine
  作者：C Bienvenu、C Lebrun、J Cadet

  DOI：10.1051/jcp/1997940300

  日期：——

  The 5,6-dihydroxy-5,6-dihydro-5-methyl-2’-deoxycytidine is an oxidation product formed by hydroxyl radical (^{•OH). The same product has been obtained by menadione photosensitization of 5-methyl-2’-deoxycytidine (m5dCyd). 18O labeling experiments led us to suggest a mechanism for the photosensitized formation of 5,6-dihydroxy-5,6-dihydro-5-methyl-2’-deoxycytidine involving initial generation of the m5dCyd radical cation.}

  5,6-二羟基-5,6-二氢-5-甲基-2’-脱氧胞苷是羟基自由基(^{•OH)形成的氧化产物。通过甲萘醌光敏化 5-甲基-2’-脱氧胞苷 (m5dCyd) 获得了相同的产物。 18O 标记实验使我们提出了 5,6-二羟基-5,6-二氢-5-甲基-2'-脱氧胞苷的光敏形成机制，涉及 m5dCyd 自由基阳离子。}

表征谱图