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-glucopyranosyl trichloroacetimidate | 1344089-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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-glucopyranosyl trichloroacetimidate
• 英文别名: Glc2Ac3Ac4Ac6Ac(b1-4)[Ara2Ac3Ac4Ac(a1-6)]Glc2Ac3Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-[[(2R,3R,4S,5S)-3,4,5-triacetyloxyoxan-2-yl]oxymethyl]-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1344089-21-9
• 化学式: C₃₇H₄₈Cl₃NO₂₄
• 分子量: 997.139
• InChiKey: TUUUYCQKVNZPBG-VBEQRUIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  65
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  316
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  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-glucopyranosyl trichloroacetimidate 、 菝葜皂苷元 在 三氟甲磺酸三甲基硅酯 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 、 methanool 为溶剂， 反应 3.67h， 以89%的产率得到sarsasapogenyl β-D-glucopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->6)]-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：

  、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以126 mg的产率得到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-glucopyranosyl trichloroacetimidate
  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