25,27-Dihydroxy-26-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)oxy-28-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxycalix[4]arene | 163251-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 25,27-Dihydroxy-26-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)oxy-28-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxycalix[4]arene
• CAS: 163251-60-3
• 化学式: C₅₆H₆₀O₂₂
• 分子量: 1085.08
• InChiKey: LWVUFEGKNGHGJU-SFNPMHINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  78.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  287.78
• 氢给体数：
  2.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  25,27-Dihydroxy-26-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)oxy-28-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxycalix[4]arene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 25-(α-D-Glucopyranosyl)oxy-27-(β-D-glucopyranosyl)oxy-26,28-dihydroxycalix[4]arene
  参考文献：
  名称：

  Marra, Alberto; Scherrmann, Marie-Christine; Dondoni, Alessandro, Angewandte Chemie, 1994, vol. 106, # 23/24, p. 2533 - 2535

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 、 杯[4]芳烃 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以16%的产率得到25,27-Dihydroxy-26,28-bis[(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)oxy]calix[4]arene
  参考文献：
  名称：

  Synthesis and Properties ofO-Glycosyl Calix[4]Arenes (Calixsugars)

  摘要：

  AbstractModelO‐glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate‐containing calixarene derivatives named calixsugars. One or two sugar moieties (D‐mannofuranose and D‐glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]arenes bearing two or four hydroxymethyl groups at the upper rim were coupled with perbenzoylated thioethyl D‐galactoside and D‐lactoside in the presence of the thiophilic promoter copper(III) triflate. In this way β‐linked bis‐ and tetrakis‐O‐galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For theO‐lactosyl derivatives only the bis‐substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3‐hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose‐containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.

  DOI：

  10.1002/chem.19970031108