6¹-S-α-maltosyl-6-thiocyclomaltoheptaose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6¹-S-α-maltosyl-6-thiocyclomaltoheptaose
• 英文别名: (1S,3R,5R,6S,8S,10S,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-10-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylmethyl]-5,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• 化学式: C₅₄H₉₀O₄₄S
• 分子量: 1475.35
• InChiKey: BVPLVSVMZZVMQV-IZKORWIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -18
• 重原子数：
  99
• 可旋转键数：
  13
• 环数：
  23.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  728
• 氢给体数：
  27
• 氢受体数：
  45

反应信息

• 作为产物：
  描述：

  1-thio-α-maltose sodium salt 、 mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 在 N,N-二甲基丙烯基脲 作用下， 反应 18.0h， 以65%的产率得到6¹-S-α-maltosyl-6-thiocyclomaltoheptaose
  参考文献：
  名称：

  Inclusion and solubilization properties of 6-S-glycosyl-6-thio derivatives of β-cyclodextrin

  摘要：

  The synthesis and physico-chemical properties of branched beta-cyclodextrins substituted by one or seven thioglycoside units at the primary hydroxy side are described. The solubilities in water of these compounds are strongly increased compared with the parent beta-cyclodextrin although large differences are found between alpha- and beta-anomers, the former exhibiting the larger solubility. The inclusion capacity of these derivatives has been investigated using NMR spectroscopy as the major analytical technique for various host-guest pairs. The apparent discrepancies between the intrinsic solubilities of these host molecules and their ability to solubilize hydrophobic hosts can be explained from geometrical considerations derived from detailed NMR studies. The respective roles of the:side of inclusion, of steric effects and of stabilizing interactions are evidenced and allow an a priori selection of the optimal host derivative for a given guest molecule.

  DOI：

  10.1039/p29950001479

文献信息

• Inclusion and solubilization properties of 6-S-glycosyl-6-thio derivatives of β-cyclodextrin
  作者：Valérié Lainé、Annie Coste-Sarguet、Andrée Gadelle、Jacques Defaye、Bruno Perly、Florence Djedaïni-Pilard

  DOI：10.1039/p29950001479

  日期：——

  The synthesis and physico-chemical properties of branched beta-cyclodextrins substituted by one or seven thioglycoside units at the primary hydroxy side are described. The solubilities in water of these compounds are strongly increased compared with the parent beta-cyclodextrin although large differences are found between alpha- and beta-anomers, the former exhibiting the larger solubility. The inclusion capacity of these derivatives has been investigated using NMR spectroscopy as the major analytical technique for various host-guest pairs. The apparent discrepancies between the intrinsic solubilities of these host molecules and their ability to solubilize hydrophobic hosts can be explained from geometrical considerations derived from detailed NMR studies. The respective roles of the:side of inclusion, of steric effects and of stabilizing interactions are evidenced and allow an a priori selection of the optimal host derivative for a given guest molecule.