N-(6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)-N'-(2,3,4,2',3',4'-hexa-O-acetyl-6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)thiourea | 1016980-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)-N'-(2,3,4,2',3',4'-hexa-O-acetyl-6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)thiourea
• CAS: 1016980-00-9
• 化学式: C₃₇H₅₄N₈O₂₄S
• 分子量: 1026.94
• InChiKey: DAJIUJXLWWWCJJ-OQDFASIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.24
• 重原子数：
  70.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  456.14
• 氢给体数：
  8.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  N-(6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)-N'-(2,3,4,2',3',4'-hexa-O-acetyl-6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)thiourea 在 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以99%的产率得到N,N'-bis-(6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)thiourea
  参考文献：
  名称：

  Synthesis, Structure, and Inclusion Capabilities of Trehalose-Based Cyclodextrin Analogues (Cyclotrehalans)

  摘要：

  Concise and efficient strategies toward the synthesis of D-2h- and D-3h-symmetric cyclodextrin analogues alternating alpha,alpha'-trehalose disaccharide subunits and pseudoamide segments (cyclotrehalans, CTs) are reported. The conformational properties of these cyclooligosaccharides are governed by the rigidity of the alpha,alpha'-trehalose disaccharide repeating unit and the partial double-bond character of the N-(C=X) linkages. In contrast to the typical concave-shaped cavity of cyclodextrins (CDs), CTs feature a convex-shaped hydrophobic cavity in which the beta-face of the monosaccharide subunits is oriented toward the inner side, as supported by NMR and modeling (molecular mechanics and dynamics) studies. In the case of cyclodimeric CTs (CT2s), the existence of intramolecular hydrogen bonds results in collapsed cavities, too small to allow the formation of inclusion complexes with organic molecules. Cyclotrimeric CTs (CT3s) display cavity sizes that are intermediate between those of alpha CD and beta CD, ideally suited for the complexation of complementary guests with ternary symmetry such as adamantane 1-carboxylate (AC). The higher flexibility of the pseudoamide bridges as compared with classical glycosidic linkages endow these glyconanocavities with some conformational adaptability properties, making them better suited than CDs for complexation of angular guests, as seen from comparative inclusion capability experiments against the fluorescent probes 6-p-toluidinonaphthalene-2-sulfonate (TNS; linear) and 8-anilinonaphthalene-1-sulfonate (ANS; angular).

  DOI：

  10.1021/jo800048s
• 作为产物：
  描述：

  6-amino-6'-azido-6,6'-dideoxy-α,α'-trehalose 、 2,3,4,2',3',4'-hexa-O-acetyl-6-azido-6,6'-dideoxy-6'-isothiocyanato-α,α'-trehalose 在 吡啶 作用下， 反应 16.0h， 以78%的产率得到N-(6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)-N'-(2,3,4,2',3',4'-hexa-O-acetyl-6'-azido-6,6'-dideoxy-α,α'-trehalos-6-yl)thiourea
  参考文献：
  名称：

  Synthesis, Structure, and Inclusion Capabilities of Trehalose-Based Cyclodextrin Analogues (Cyclotrehalans)

  摘要：

  Concise and efficient strategies toward the synthesis of D-2h- and D-3h-symmetric cyclodextrin analogues alternating alpha,alpha'-trehalose disaccharide subunits and pseudoamide segments (cyclotrehalans, CTs) are reported. The conformational properties of these cyclooligosaccharides are governed by the rigidity of the alpha,alpha'-trehalose disaccharide repeating unit and the partial double-bond character of the N-(C=X) linkages. In contrast to the typical concave-shaped cavity of cyclodextrins (CDs), CTs feature a convex-shaped hydrophobic cavity in which the beta-face of the monosaccharide subunits is oriented toward the inner side, as supported by NMR and modeling (molecular mechanics and dynamics) studies. In the case of cyclodimeric CTs (CT2s), the existence of intramolecular hydrogen bonds results in collapsed cavities, too small to allow the formation of inclusion complexes with organic molecules. Cyclotrimeric CTs (CT3s) display cavity sizes that are intermediate between those of alpha CD and beta CD, ideally suited for the complexation of complementary guests with ternary symmetry such as adamantane 1-carboxylate (AC). The higher flexibility of the pseudoamide bridges as compared with classical glycosidic linkages endow these glyconanocavities with some conformational adaptability properties, making them better suited than CDs for complexation of angular guests, as seen from comparative inclusion capability experiments against the fluorescent probes 6-p-toluidinonaphthalene-2-sulfonate (TNS; linear) and 8-anilinonaphthalene-1-sulfonate (ANS; angular).

  DOI：

  10.1021/jo800048s