4-methoxyphenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside | 1344089-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside
• 英文别名: Ara2Ac3Ac4Ac(a1-6)Glc2Ac3Ac(b)-O-Ph(4-OMe)；[(3S,4S,5R,6R)-4,5-diacetyloxy-6-[[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-3-hydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methoxy]oxan-3-yl] acetate
• CAS: 1344089-17-3
• 化学式: C₂₈H₃₆O₁₆
• 分子量: 628.584
• InChiKey: OBLTVKDUBDFBQI-MDADQXGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside 、 2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以66%的产率得到4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6)]-2,3-di-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis and antitumor activities of trisaccharide steroidal saponins

  摘要：

  The naturally derived trisaccharide steroidal saponin 1 and structurally modified derivatives 2 and 3 bearing the same sarsasapogenin aglycon were synthesized concisely via a direct transglycosylation strategy. The antitumor activities of the synthetic trisaccharide saponins 1-3 and their corresponding a-isomers 1a-3a were preliminarily evaluated against human gastric adenocarcinoma cell (MKN-45) and human epithelial cervical cancer cell (HeLa) by CCK-8 assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.026
• 作为产物：
  描述：

  p-methoxyphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-methoxyphenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis and antitumor activities of trisaccharide steroidal saponins

  摘要：

  The naturally derived trisaccharide steroidal saponin 1 and structurally modified derivatives 2 and 3 bearing the same sarsasapogenin aglycon were synthesized concisely via a direct transglycosylation strategy. The antitumor activities of the synthetic trisaccharide saponins 1-3 and their corresponding a-isomers 1a-3a were preliminarily evaluated against human gastric adenocarcinoma cell (MKN-45) and human epithelial cervical cancer cell (HeLa) by CCK-8 assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.026