2-tetradecylhexadecyl O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1-4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-β-D-glucopyranoside | 195712-32-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-tetradecylhexadecyl O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1-4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-5-benzoyloxy-6-[(2R,3R,4S,5R,6R)-5-benzoyloxy-2-(benzoyloxymethyl)-6-(2-tetradecylhexadecoxy)-4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methyl benzoate
• CAS: 195712-32-4
• 化学式: C₈₂H₁₁₄O₂₂
• 分子量: 1451.79
• InChiKey: HUZSIPAMEQSLEH-QMCYUZPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.9
• 重原子数：
  104
• 可旋转键数：
  53
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  280
• 氢给体数：
  2
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  三氧化硫吡啶 、 2-tetradecylhexadecyl O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1-4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-β-D-glucopyranoside 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到
  参考文献：
  名称：

  A Highly Practical Synthesis of Sulfated Lewis X:  One-Pot, Two-Step Glycosylation Using “Armed/Disarmed” Coupling and Selective Benzoylation and Sulfation

  摘要：

  In spite of the several attractive biological activities of the Le(x), sLe(x), and sulfated Le(x) derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le(x) analogs and succeeded in establishing highly practical syntheses of the Le(x) and sulfated Le(x) analogs. Especially, the ''armed/disarmed'' method allowed the first synthesis of Le(x) derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le(x), sulfated Le(x), and other derivatives.

  DOI：

  10.1021/jo970076m
• 作为产物：
  描述：

  2-tetradecylhexadecyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-β-D-glucopyranoside 在 溶剂黄146 作用下， 反应 4.0h， 以88%的产率得到2-tetradecylhexadecyl O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1-4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  A Highly Practical Synthesis of Sulfated Lewis X:  One-Pot, Two-Step Glycosylation Using “Armed/Disarmed” Coupling and Selective Benzoylation and Sulfation

  摘要：

  In spite of the several attractive biological activities of the Le(x), sLe(x), and sulfated Le(x) derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le(x) analogs and succeeded in establishing highly practical syntheses of the Le(x) and sulfated Le(x) analogs. Especially, the ''armed/disarmed'' method allowed the first synthesis of Le(x) derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le(x), sulfated Le(x), and other derivatives.

  DOI：

  10.1021/jo970076m