(2R,3S,4S,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)oxy)-5-(prop-2-yn-1-yloxy)tetrahydro-2H-pyran | 674777-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)oxy)-5-(prop-2-yn-1-yloxy)tetrahydro-2H-pyran
• CAS: 674777-78-7
• 化学式: C₆₄H₆₆O₁₂
• 分子量: 1027.22
• InChiKey: QPNLHXTYBHYUKC-UFSRNXKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  76.0
• 可旋转键数：
  27.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  110.76
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)oxy)-5-(prop-2-yn-1-yloxy)tetrahydro-2H-pyran 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 生成 、 Bn(-2)[Bn(-3)][prop-2-ynyl(-4)][Bn(-6)]Man(a1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Man
  参考文献：
  名称：

  Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide

  摘要：

  A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.

  DOI：

  10.1021/ja039374t
• 作为产物：
  描述：

  p-methoxyphenyl-4,6-O-benzylidene-2,3-O-benzyl-α-D-mannopyranoside 在 三乙基硅烷 、 三氟甲磺酸酐 、 二苯基亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.17h， 生成 (2R,3S,4S,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yl)oxy)-5-(prop-2-yn-1-yloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide

  摘要：

  A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.

  DOI：

  10.1021/ja039374t