allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-α-D-glucopyranoside | 607364-85-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-α-D-glucopyranoside
• CAS: 607364-85-2
• 化学式: C₄₉H₄₄O₁₅
• 分子量: 872.879
• InChiKey: IUFVWGSLPCPIGK-RCUVKPMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  64.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  188.65
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 、 allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以80.4%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)]-2,6-di-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Laminarin Oligosaccharide Derivatives Havingd‐Arabinofuranosyl Side‐Chains

  摘要：

  An efficient glycosylation strategy was applied in the synthesis of beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->4)]-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->6)]-D-glucopyranose to secure beta-D-(1-->3) glycosidic bond formation between glucopyranosyl residues. The new strategy using a 4,6-O-benzylidenated acceptor avoided generation of the alpha major isomer in the attempted beta-D-(1-->3) glycosylation under standard glycosylation conditions. The hexasaccharide we prepared showed about 30% tumor growth inhibition towards S180 model study.

  DOI：

  10.1081/car-120023470
• 作为产物：
  描述：

  allyl 2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Laminarin Oligosaccharide Derivatives Havingd‐Arabinofuranosyl Side‐Chains

  摘要：

  An efficient glycosylation strategy was applied in the synthesis of beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->4)]-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->6)]-D-glucopyranose to secure beta-D-(1-->3) glycosidic bond formation between glucopyranosyl residues. The new strategy using a 4,6-O-benzylidenated acceptor avoided generation of the alpha major isomer in the attempted beta-D-(1-->3) glycosylation under standard glycosylation conditions. The hexasaccharide we prepared showed about 30% tumor growth inhibition towards S180 model study.

  DOI：

  10.1081/car-120023470