1-[[(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]methyl]-3-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-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]-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]thiourea | 1141510-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[[(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]methyl]-3-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-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]-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]thiourea
• CAS: 1141510-48-6
• 化学式: C₃₈H₆₄N₁₀O₂₇S₂
• 分子量: 1157.11
• InChiKey: ITKILMDBOUNFLI-ALYQPIBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.7
• 重原子数：
  77
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  588
• 氢给体数：
  22
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 1-[[(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]methyl]-3-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-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]-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]thiourea 在 吡啶 、 六甲基二硅氮烷 作用下， 反应 16.0h， 以80%的产率得到1-[[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]oxy-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methyl]-3-[[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[[[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]oxy-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methylcarbamothioylamino]methyl]-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]oxy-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methyl]thiourea
  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：

  [(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 在 sodium methylate 、 水 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以100%的产率得到1-[[(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]methyl]-3-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-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]-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]thiourea
  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