allyl 5-O-acetyl-2-deoxy-2-p-thiotolyl-β-D-xylofuranoside | 1187662-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 5-O-acetyl-2-deoxy-2-p-thiotolyl-β-D-xylofuranoside
• CAS: 1187662-59-4
• 化学式: C₁₇H₂₂O₅S
• 分子量: 338.425
• InChiKey: RQMOLKVQGWFDKY-YYIAUSFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 5-O-acetyl-2-deoxy-2-p-thiotolyl-β-D-xylofuranoside 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 5.0h， 以100%的产率得到allyl 3,5-di-O-acetyl-2-deoxy-2-p-thiotolyl-β-D-xylofuranoside
  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：

  、 烯丙醇 在 samarium(III) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到allyl 5-O-acetyl-2-deoxy-2-p-thiotolyl-β-D-xylofuranoside
  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