6-amino-6'-azido-6,6'-dideoxy-α,α'-trehalose | 1016979-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-amino-6'-azido-6,6'-dideoxy-α,α'-trehalose
• 英文别名: (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(2R,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-3,4,5-triol
• CAS: 1016979-90-0
• 化学式: C₁₂H₂₂N₄O₉
• 分子量: 366.328
• InChiKey: FGYXVKCUBWBFAV-LIZSDCNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  189
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-amino-6'-azido-6,6'-dideoxy-α,α'-trehalose 、 2,3,4,2',3',4'-hexa-O-acetyl-6,6'-dideoxy-6,6'-diisothiocyanato-α,α'-trehalose 在 吡啶 作用下， 反应 16.0h， 以75%的产率得到[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-[[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methylcarbamothioylamino]methyl]-6-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methylcarbamothioylamino]methyl]oxan-2-yl]oxyoxan-3-yl] acetate
  参考文献：
  名称：

  Size-Tunable Trehalose-Based Nanocavities: Synthesis, Structure, and Inclusion Properties of Large-Ring Cyclotrehalans

  摘要：

  [GRAPHICS]An efficient strategy toward the synthesis of large-ring cyclodextrin (CD) analogs alternating alpha,alpha'-trehalose disaccharide subunits and pseudoamide segments (cyclotrehalans, CTs), involving a bimolecular macrocyclization reaction as the key step, is reported. NMR and molecular modeling confirmed that the eight and ten alpha-D-glucopyranoside subunits in tetrameric and pentameric CT homologues (CT4 and CT5, respectively) are magnetically equivalent, as in the gamma and epsilon CD counterparts. Yet, the orientation of the monosaccharide constituents is reversed in CTs as compared with CDs, the beta-face being directed to the inside of the nanometric cavity while the alpha-face remains in contact with the bulk solvent. Molecular mechanics and dynamics experiments revealed that the cyclooligosaccharide architecture in CT4 and CT5 is relatively flexible, which is in contrast to that previously observed for the first members of the CT series (CT2 and CT3 oligomers). Thus, although in their fully expanded conformation their cavity size is close to that of gamma CD, the higher mobility of the pseudoamide bridges as compared with classical glycosidic linkages endows these hosts with induced fitting capabilities toward smaller guests.

  DOI：

  10.1021/jo802796p
• 作为产物：
  描述：

  6,6'-diazido-6,6'-dideoxy-α,α-trehalose 在 1,3-丙二硫醇 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 5.0h， 以41%的产率得到6-amino-6'-azido-6,6'-dideoxy-α,α'-trehalose
  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