allyl (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside | 583043-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside
• 英文别名: allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside
• CAS: 583043-07-6
• 化学式: C₆₄H₅₄O₁₈
• 分子量: 1111.12
• InChiKey: XAIRXCHZSOQQSY-ONEYLHGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  82.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  allyl (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  First syntheses of d-mannose penta- and decasaccharides, the repeating unit and its dimer of the cell-wall mannan of Candida kefyr IFO 0586

  摘要：

  alpha-D-Mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranose and alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)]-alpha-D-marmopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranose, the repeating unit and its dimer of the cell wall mannan of the pathogenic yeast Candida kefyr IFO 0586, have been efficiently synthesized via their allyl glycosides by using allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside, allyl 6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranoside, and allyl 3,4-di-O-benzoyl-alpha-D-mannopyranoside as synthons. The blocked pentasaccharide was regio- and stereoselectively prepared by coupling of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranoside with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, and then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate in a one-pot manner. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00216-7
• 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 3,4,6-tri-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到allyl (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  DNA模板的肽核酸编码的寡糖的同源和异源二聚化作用，模仿了HIV的碳水化合物表位

  摘要：

  全部受控制：杂交的可编程性已用于生成结构的组合文库，该文库模拟复杂碳水化合物与抗体相互作用的拓扑结构，该抗体显示出针对HIV的广谱活性。这种简单的方法涉及以受控方式将标记有肽核酸的寡糖附着到DNA模板上（请参见示意图）。

  DOI：

  10.1002/anie.200903328