[(1R,3R,4R,5S,6R,7R,13R,14S,15S,16R,17R,19R,20R,21S,22S,23R,29R,30R,31S,32R)-4,5,30,31,32-pentaacetyloxy-14,15,16,20,21,22-hexahydroxy-10,26-bis(sulfanylidene)-2,18,33,34,35,36-hexaoxa-9,11,25,27-tetrazapentacyclo[27.3.1.13,7.113,17.119,23]hexatriacontan-6-yl] acetate | 162019-31-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,3R,4R,5S,6R,7R,13R,14S,15S,16R,17R,19R,20R,21S,22S,23R,29R,30R,31S,32R)-4,5,30,31,32-pentaacetyloxy-14,15,16,20,21,22-hexahydroxy-10,26-bis(sulfanylidene)-2,18,33,34,35,36-hexaoxa-9,11,25,27-tetrazapentacyclo[27.3.1.13,7.113,17.119,23]hexatriacontan-6-yl] acetate
• CAS: 162019-31-0
• 化学式: C₃₈H₅₆N₄O₂₄S₂
• 分子量: 1017.01
• InChiKey: QWLVIDWTYRFXLT-OQDFASIVSA-N

物化性质

• 沸点：
  1003.0±75.0 °C(predicted)
• 密度：
  1.59±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  68
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  447
• 氢给体数：
  10
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  [(1R,3R,4R,5S,6R,7R,13R,14S,15S,16R,17R,19R,20R,21S,22S,23R,29R,30R,31S,32R)-4,5,30,31,32-pentaacetyloxy-14,15,16,20,21,22-hexahydroxy-10,26-bis(sulfanylidene)-2,18,33,34,35,36-hexaoxa-9,11,25,27-tetrazapentacyclo[27.3.1.13,7.113,17.119,23]hexatriacontan-6-yl] acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, conformational flexibility and preliminary complexation behaviour of α,α′-trehalose-based macrocycles containing thiourea spacers

  摘要：

  报告了一种高效合成大环配体的方法，该配体包含两个δ,δâ²-三卤糖亚基，通过 1,3-thiourea 间隔物在主 C-6,6â²位置连接；NâC(S) 键的 Z/E 构型受分子内氢键和立体因素的影响。

  DOI：

  10.1039/c39950000057
• 作为产物：
  描述：

  海藻糖 在 吡啶 作用下， 生成 [(1R,3R,4R,5S,6R,7R,13R,14S,15S,16R,17R,19R,20R,21S,22S,23R,29R,30R,31S,32R)-4,5,30,31,32-pentaacetyloxy-14,15,16,20,21,22-hexahydroxy-10,26-bis(sulfanylidene)-2,18,33,34,35,36-hexaoxa-9,11,25,27-tetrazapentacyclo[27.3.1.13,7.113,17.119,23]hexatriacontan-6-yl] acetate
  参考文献：
  名称：

  Synthesis, conformational flexibility and preliminary complexation behaviour of α,α′-trehalose-based macrocycles containing thiourea spacers

  摘要：

  报告了一种高效合成大环配体的方法，该配体包含两个δ,δâ²-三卤糖亚基，通过 1,3-thiourea 间隔物在主 C-6,6â²位置连接；NâC(S) 键的 Z/E 构型受分子内氢键和立体因素的影响。

  DOI：

  10.1039/c39950000057

文献信息

• Synthesis, Structure, and Inclusion Capabilities of Trehalose-Based Cyclodextrin Analogues (Cyclotrehalans)
  作者：David Rodríguez-Lucena、Juan M. Benito、Eleuterio Álvarez、Carlos Jaime、Javier Perez-Miron、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/jo800048s

  日期：2008.4.1

  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).