allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)]-3,4-di-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside | 474959-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)]-3,4-di-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
• CAS: 474959-42-7
• 化学式: C₁₁₃H₉₆O₃₄
• 分子量: 1997.98
• InChiKey: ATELTPFKODSGJL-WPGOZHNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.41
• 重原子数：
  147.0
• 可旋转键数：
  38.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  415.74
• 氢给体数：
  0.0
• 氢受体数：
  34.0

反应信息

• 作为反应物：
  描述：

  allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)]-3,4-di-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以96%的产率得到allyl 2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)]-3,4-di-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  A highly efficient synthesis of an octasaccharide, the repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum

  摘要：

  A highly concise and effective synthesis of the mannose octasaccharide repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum was achieved via 6-O-glycosylation of a tetrasaccharide acceptor with a tetrasaccharide donor, followed by deprotection. The key tetrasaccharide (11) was constructed by selective 6-O-glycosylation of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside with 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate. The tetrasaccharide acceptor (13) was obtained by selective 6-O-deacetylation of 11, while the tetrasaccharide donor 12 was obtained by deallylation of 11, followed by trichloroacetimidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00117-9
• 作为产物：
  描述：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 、 allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-3,4-di-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)]-3,4-di-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  A highly efficient synthesis of an octasaccharide, the repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum

  摘要：

  A highly concise and effective synthesis of the mannose octasaccharide repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum was achieved via 6-O-glycosylation of a tetrasaccharide acceptor with a tetrasaccharide donor, followed by deprotection. The key tetrasaccharide (11) was constructed by selective 6-O-glycosylation of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside with 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate. The tetrasaccharide acceptor (13) was obtained by selective 6-O-deacetylation of 11, while the tetrasaccharide donor 12 was obtained by deallylation of 11, followed by trichloroacetimidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00117-9