p-methoxyphenyl 1-thio-α-D-arabinofuranoside | 1187662-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 1-thio-α-D-arabinofuranoside
• 英文别名: (2R,3S,4S,5R)-2-(hydroxymethyl)-5-(4-methoxyphenyl)sulfanyloxolane-3,4-diol
• CAS: 1187662-67-4
• 化学式: C₁₂H₁₆O₅S
• 分子量: 272.322
• InChiKey: ZRBDEMYVMIMBOF-WISYIIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 1-thio-α-D-arabinofuranoside 、 苯甲酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到p-methoxyphenyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside
  参考文献：
  名称：

  2,3-Anhydrosugars in Glycoside Bond Synthesis: Mechanism of 2-Deoxy-2-thioaryl Glycoside Formation

  摘要：

  A series of investigations probing the mechanism of the 2,3-anhydrosugar migration-glycosylation reaction were performed using a thioglycoside with the D-lyxo stereochemistry as the substrate. Among the work reported are the results of quantum mechanical calculations, NMR studies, the measurement of a-deuterium kinetic isotope effects, and the synthesis of a series of substrate analogues. All studies point to a consistent finding: that the reaction proceeds through an oxocarbenium ion intermediate, not an episulfonium ion as previously suggested. It is proposed that the high stereoselectivity of the reaction arises from a preferred "inside attack" of the nucleophile onto the oxocarbenium ion intermediate.

  DOI：

  10.1021/ja9029945
• 作为产物：
  描述：

  p-methoxyphenyl 2,3,5-tri-O-benzoyl-1-thio-α-D-arabinofuranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以91%的产率得到p-methoxyphenyl 1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  2,3-Anhydrosugars in Glycoside Bond Synthesis: Mechanism of 2-Deoxy-2-thioaryl Glycoside Formation

  摘要：

  A series of investigations probing the mechanism of the 2,3-anhydrosugar migration-glycosylation reaction were performed using a thioglycoside with the D-lyxo stereochemistry as the substrate. Among the work reported are the results of quantum mechanical calculations, NMR studies, the measurement of a-deuterium kinetic isotope effects, and the synthesis of a series of substrate analogues. All studies point to a consistent finding: that the reaction proceeds through an oxocarbenium ion intermediate, not an episulfonium ion as previously suggested. It is proposed that the high stereoselectivity of the reaction arises from a preferred "inside attack" of the nucleophile onto the oxocarbenium ion intermediate.

  DOI：

  10.1021/ja9029945