p-methoxybenzyl 2,3,5-tri-O-benzoyl-1-thio-α-D-arabinofuranoside | 1187662-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxybenzyl 2,3,5-tri-O-benzoyl-1-thio-α-D-arabinofuranoside
• CAS: 1187662-65-2
• 化学式: C₃₄H₃₀O₈S
• 分子量: 598.673
• InChiKey: BGHMVEQETMMSLN-HEFUCBFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl 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89%的产率得到p-methoxybenzyl 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
• 作为产物：
  描述：

  4-甲氧基苄硫醇 、 methyl tri-O-benzoyl-α-D-arabinofuranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 以74%的产率得到p-methoxybenzyl 2,3,5-tri-O-benzoyl-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