p-methoxyphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside | 1009006-53-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: 4-methoxyphenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-β-D-glucopyranoside；[(2R,4aR,6S,7R,8S,8aR)-7-acetyloxy-6-(4-methoxyphenoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS: 1009006-53-4
• 化学式: C₂₄H₂₆O₉
• 分子量: 458.465
• InChiKey: BYOYUZZNZMTKKG-UNBXWCMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 在 ammonium cerium (IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 水 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.84h， 生成 sarsasapogenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6)]-3-O-acetyl-α-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：

  1,2,3-tri-O-acetyl-4,6-O-benzylidene-D-glucopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 p-methoxyphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  JP6273199

  摘要：

  公开号：

文献信息

• <i>O</i>- and <i>N</i>-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Laura J. Ingram、Ahmed Desoky、Ahmed M. Ali、Scott D. Taylor

  DOI：10.1021/jo9014112

  日期：2009.9.4

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.