[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-2-yl]methyl acetate | 181427-61-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-2-yl]methyl acetate
• CAS: 181427-61-2
• 化学式: C₂₄H₃₃N₅O₂₀P₂
• 分子量: 773.495
• InChiKey: HNHNUWHRTUYSBJ-YZNBHSQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  352
• 氢给体数：
  6
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-2-yl]methyl acetate 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 guanosine 5'-diphospho-D-mannose
  参考文献：
  名称：

  Stereoselective Chemical Synthesis of Sugar Nucleotides via Direct Displacement of Acylated Glycosyl Bromides

  摘要：

  The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-alpha-d-mannose as well as UDP- and GDP-beta-l-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates.

  DOI：

  10.1021/ol063068d
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 3 A molecular sieve 、 三溴化磷 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.75h， 生成 [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Stereoselective Chemical Synthesis of Sugar Nucleotides via Direct Displacement of Acylated Glycosyl Bromides

  摘要：

  The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-alpha-d-mannose as well as UDP- and GDP-beta-l-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates.

  DOI：

  10.1021/ol063068d