hexakis(2,3-di-O-benzyl)-α-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexakis(2,3-di-O-benzyl)-α-cyclodextrin
• 英文别名: 2^I,3^I,2^II,3^II,2^III,3^III,2^IV,3^IV,2^V,3^V,2^VI,3^VI-dodeca-O-benzyl-maltocyclohexaose；per-2,3-di-O-benzyl-α-cyclodextrin；[(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,32R,33S,34R,35S,36R,37S,38R,39S,40R,41S,42R)-10,15,20,25,30-pentakis(hydroxymethyl)-31,32,33,34,35,36,37,38,39,40,41,42-dodecakis(phenylmethoxy)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontan-5-yl]methanol
• 化学式: C₁₂₀H₁₃₂O₃₀
• 分子量: 2054.35
• InChiKey: IYVLOANQDZCDBM-YZDTYKPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  150
• 可旋转键数：
  42
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  343
• 氢给体数：
  6
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  hexakis(2,3-di-O-benzyl)-α-cyclodextrin 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以100%的产率得到α-环糊精
  参考文献：
  名称：

  Chemical Synthesis of Cyclodextrins by Using Intramolecular Glycosylation

  摘要：

  An efficient synthesis of cyclodextrins (CDs) by using the intramolecular glycosylation is demonstrated. alpha-CD, an alpha(1-->4)linked hexaglucoside, was prepared via a block condensation of three maltose units. A modified key maltose intermediate as a precursor to both glycosyl donor and acceptor components was prepared in 6 steps starting from maltose. All the glycosylation for chain elongation and cyclization of saccharides was carried out after tethering the donor to the acceptor by the phthaloyl bridge to give the desired saccharides in good yields with complete alpha-selectivity. delta-CD composed of 9 glucose units was synthesized by the same manner from three maltotriose units.

  DOI：

  10.1021/jo025887r
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 hexakis(2,3-di-O-benzyl)-α-cyclodextrin
  参考文献：
  名称：

  Hyper-crosslinked cyclodextrin porous polymer: an efficient CO₂ capturing material with tunable porosity

  摘要：

  设计并合成了几种基于环糊精（CD）的超交联多孔聚合物（HCPPs），用于选择性CO₂吸附和储存。还建立了一种可行的方法来调节材料的孔隙度。

  DOI：

  10.1039/c6ra18307g

文献信息

• Synthesis of 2,3-O-dibenzyl-6-O-sulfobutyl-α and β cyclodextrins: new chiral surfactants for capillary electrophoresis
  作者：James A. McKee、Thomas K. Green

  DOI：10.1016/j.tetlet.2015.05.057

  日期：2015.7

  heptakis(2,3-O-dibenzyl-6-O-sulfobutyl)cyclomaltoheptaose were synthesized in four steps. Pyrene fluorescence studies indicate micelle formation at 90 μM in water for both modified cyclodextrins (CDs). Both CDs offer potential as chiral micellar selectors for enantiomeric separations using capillary electrophoresis. Sodium heptakis(2,3-O-dibenzyl-6-O-sulfobutyl)cyclomaltoheptaose baseline resolved fluorescent

  两亲性钠六（2,3- ö二苄基-6- ö -sulfobutyl）cyclomaltohexaose和钠heptakis（2,3- ö二苄基-6- ö -sulfobutyl）cyclomaltoheptaose在四个步骤合成。fluorescence荧光研究表明，两种修饰的环糊精（CD）均在90μM的水中形成胶束。两种CD均可作为手性胶束选择剂，用于使用毛细管电泳进行对映体分离。七/（2,3 - O-二苄基-6 - O-磺基丁基）环麦芽庚糖钠基线解析的d / l-丝氨酸荧光氰基苄基吲哚（CBI）衍生物，浓度为50-200μM。
• Cyanoethylation of cyclodextrin derivatives
  作者：Ramprasad Ghosh、Moulimala Bhowmick、Ping Zhang、Chang-Chun Ling

  DOI：10.1139/cjc-2015-0379

  日期：2016.4

  The synthesis of novel cyanoethylated cyclodextrin derivatives from previously prepared intermediates is described. It was found the alcohols at the primary face of cyclodextrins readily react to add to acrylonitrile, but similar additions from hydroxyl groups of the secondary face appear to be more difficult. The obtained cyanides could be reduced to form the corresponding amines.

  描述了从先前制备的中间体合成新型氰乙基化环糊精衍生物。发现在环糊精的主面上的醇很容易反应添加到丙烯腈中，但从第二面上的羟基进行类似的添加似乎更困难。得到的氰化物可以还原形成相应的胺。
• Hyper-crosslinked cyclodextrin porous polymer: an efficient CO₂ capturing material with tunable porosity
  作者：Bo Meng、Haiying Li、Shannon M. Mahurin、Honglai Liu、Sheng Dai

  DOI：10.1039/c6ra18307g

  日期：——

  Several cyclodextrin (CD)-based hyper-crosslinked porous polymers (HCPPs) were designed and synthesized for selective CO₂ adsorption and storage. A feasible way to tailor the porosity of the materials was also established.

  设计并合成了几种基于环糊精（CD）的超交联多孔聚合物（HCPPs），用于选择性CO₂吸附和储存。还建立了一种可行的方法来调节材料的孔隙度。
• A study of the DIBAL-promoted selective debenzylation of α-cyclodextrin protected with two different benzyl groups
  作者：Naser-Abdul Yousefi、Morten L Zimmermann、Mikael Bols

  DOI：10.3762/bjoc.18.165

  日期：——

  α-cyclodextrin protected with 2,4-dichlorobenzyl groups on the primary alcohols and ordinary benzyl groups on the secondary alcohols was prepared and subjected to DIBAL (diisobutylaluminum hydride)-promoted selective debenzylation. Debenzylation proceeded by first removing two dichlorobenzyl groups from the 6A,D positions and then removing one or two benzyl groups from the 3A,D positions.

  制备了一种用伯醇上的 2,4-二氯苄基和仲醇上的普通苄基保护的 α-环糊精，并进行 DIBAL（二异丁基氢化铝）促进的选择性脱苄基。脱苄基化首先从 6A、D 位置去除两个二氯苄基，然后从 3A、D 位置去除一个或两个苄基。
• Jullien, Ludovic; Canceill, Josette; Lacombe, Liliane, Journal of the Chemical Society. Perkin transactions II, 1994, # 5, p. 989 - 1002
  作者：Jullien, Ludovic、Canceill, Josette、Lacombe, Liliane、Lehn, Jean-Marie

  DOI：——

  日期：——