sarsasapogenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-3-O-acetyl-α-D-glucopyranoside | 1344089-33-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: sarsasapogenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-3-O-acetyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4R,5R,6S)-4-acetyloxy-5-hydroxy-6-[(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 1344089-33-3
• 化学式: C₆₃H₉₂O₂₇
• 分子量: 1281.41
• InChiKey: FTFDDQPBOLACAG-FJSXZDMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  90
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  331
• 氢给体数：
  1
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  sarsasapogenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-3-O-acetyl-α-D-glucopyranoside 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以94%的产率得到sarsasapogenyl β-D-glucopyranosyl-(1->4)-[β-D-glucopyranosyl-(1->6)]-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：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,3-di-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 、 菝葜皂苷元 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以39%的产率得到sarsasapogenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(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