O-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl-trichloracetimidate | 208709-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl-trichloracetimidate
• 英文别名: Glc2Ac3Ac4Ac6Ac(b1-3)[Araf2Ac3Ac5Ac(a1-4)]Rha2Ac(a1-2)Glc3Ac4Ac6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-5-[(2S,3R,4R,5S,6S)-3-acetyloxy-5-[(2S,3R,4S,5S)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]oxy-6-methyl-4-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 208709-48-2
• 化学式: C₄₇H₆₂Cl₃NO₃₀
• 分子量: 1227.36
• InChiKey: CSONISLFKYYTIK-QTTJLUGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  81
• 可旋转键数：
  33
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  387
• 氢给体数：
  1
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  O-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl-trichloracetimidate 、 薯蓣皂素 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 以66%的产率得到O-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-D-glucopyranosyl diosgenin
  参考文献：
  名称：

  Synthesis of Neosaponins Carrying Oligosaccharides from Natural Products

  摘要：

  DOI：

  10.3987/com-99-8612
• 作为产物：
  描述：

  allyl-O-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranoside 在 四(三苯基膦)钯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 O-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl-trichloracetimidate
  参考文献：
  名称：

  Synthesis of Neosaponins Carrying Oligosaccharides from Natural Products

  摘要：

  DOI：

  10.3987/com-99-8612

文献信息

• Chemical transglycosylation of functional bioactive glyco-linkages
  作者：Tsuyoshi Ikeda、Tetsuya Kajimoto、Junei Kinjo、Kensei Nakayama、Toshihiro Nohara

  DOI：10.1016/s0040-4039(98)00519-x

  日期：1998.5

  The natural functional bioactive oligosaccharides moieties, mimosatetraose and fabatriose, were cut off from julibrosides and soyasaponin I by chemical and enzymatic methods, respectively, and were pasted to diosgenin to give neosaponins 1 and 2. The obtained neosaponins were tested for cytotoxicity and hepatoprotective activity. This method could be applied to the synthesis of novel bioactive glycosides. (C) 1998 Elsevier Science Ltd. All rights reserved.