hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin | 68715-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin
• 英文别名: hexakis(2,3,6-tri-O-methyl)cyclomaltohexaose；permethylated α-cyclodextrin；2,3,6-Tri-O-methyl-α-cyclodextrin；hexakis(2,3,6-tri-O-methyl)-α-CD；Hexakis (2,3,6-tri-O-methyl)-|A-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)-31,32,33,34,35,36,37,38,39,40,41,42-dodecamethoxy-5,10,15,20,25,30-hexakis(methoxymethyl)-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]dotetracontane
• CAS: 68715-56-0
• 化学式: C₅₄H₉₆O₃₀
• 分子量: 1225.34
• InChiKey: YEAQKJGWTCLKJJ-PIGKAOJQSA-N

物化性质

• 溶解度：
  易溶于水、甲醇、氯仿。

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  84
• 可旋转键数：
  24
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  277
• 氢给体数：
  0
• 氢受体数：
  30

制备方法与用途

六(2,3,6-三-O-甲基)-α-环糊精是一种生物化学试剂，可用于生物材料或有机化合物，在生命科学相关研究中发挥重要作用。

反应信息

• 作为反应物：
  描述：

  hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin 生成 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-methyl-D-glucitol
  参考文献：
  名称：

  JUN, JONG-GAR;GRAY, G. R., CARBOHYDR. RES., 163,(1987) N 2, 247-261

  摘要：

  DOI：
• 作为产物：
  描述：

  Glc2Me3Me6Me(a1-4)Glc2Me3Me6Me(a1-4)Glc2Me3Me6Me(a1-4)Glc2Me3Me6Me(a1-4)Glc2Me3Me6Me(a1-4)Glc2Me3Me6Me 在 4 A molecular sieve 、 三氟化硼乙醚 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin
  参考文献：
  名称：

  A facile synthesis of novel cyclodextrin derivatives incorporating one β-(1,4)-glucosidic bond and their unique inclusion ability

  摘要：

  新型环糊精衍生物含有一个δ-(1,4)-葡糖苷键，可通过三个步骤轻松地从过甲基化的δ-和δ-环糊精中合成，与母体过甲基化的δ-和δ-环糊精相比，这种宿主分子对间硝基苯甲酸钠的包合选择性高于相应的对异构体。

  DOI：

  10.1039/b309261e
• 作为试剂：
  描述：

  L-苯丙氨酸 在 phenylalanine ammonia-lyase from Rhodotorula glutinis 、 hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin 作用下， 生成 肉桂酸
  参考文献：
  名称：

  The influence of cyclomaltooligosaccharides (cyclodextrins) on the enzymatic decomposition of l-phenylalanine catalyzed by phenylalanine ammonia-lyase

  摘要：

  Cyclomaltohexaose (alpha-cyclodextrin) and cyclomaltoheptaose (beta-cyclodextrin) as well as their four methyl ether derivatives, that is, hexakis(2,3-di-O-methyl)cyclomaltohexaose, hexakis(2,3,6-tri-O-methyl) cyclomaltohexaose, heptakis(2,3-di-O-methyl) cyclomaltoheptaose, and heptakis(2,3,6-tri-O-methyl) cyclomaltoheptaose were investigated as the additives in the course of enzymatic decomposition of L-phenylalanine catalyzed by phenylalanine ammonia-lyase. Only a few of those additives behaved like classical inhibitors of the enzymatic reaction under investigation because the values of the Michaelis constants that were obtained, as well as the maximum velocity values depended mostly atypically on the concentrations of those additives. In most cases cyclodextrins caused mixed inhibition, both competitive and noncompetitive, but they also acted as activators for selected concentrations. This atypical behaviour of cyclodextrins is caused by three different and independent effects. The inhibitory effect of cyclodextrins is connected with the decrease of substrate concentration and unfavourable influence on the flexibility of the enzyme molecules. On the other hand, the activating effect is connected with the decrease of product concentration (the product is an inhibitor of the enzymatic reaction under investigation). All these effects are caused by the ability of the cyclodextrins to form inclusion complexes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.008

文献信息

• Encapsulation of the Antioxidant R-(+)-α-Lipoic Acid in Permethylated α- and β-Cyclodextrins: Thermal and X-ray Structural Characterization of the 1:1 Inclusion Complexes
  作者：Mino Caira、Susan Bourne、Buntubonke Mzondo

  DOI：10.3390/molecules22060866

  日期：——

  between ALA and CDs motivated the present study, which describes the synthesis and X-ray structural elucidation of crystalline inclusion complexes between the biologically relevant R-(+)-α-lipoic acid (RALA) and the host molecules permethylated α-CD (TMA) and permethylated β-CD (TMB). Single crystal X-ray diffraction of TMA·RALA·6H₂O and TMB·RALA revealed significantly different orientations of the

  天然存在的化合物 α-硫辛酸 (ALA) 具有多种重要的生物学作用，其强大的抗氧化特性和治疗各种疾病的潜力使其广泛用作膳食补充剂。然而，水溶性差和热稳定性差的缺点阻碍了其作为药物的发展，促使使用环糊精（CD）来解决这些问题。关于 ALA 和 CD 之间相互作用性质的已发表的结构数据的缺乏激发了本研究，该研究描述了生物学相关的 R-(+)-α-硫辛酸之间晶体包合物的合成和 X 射线结构阐明。 RALA）和宿主分子全甲基化α-CD（TMA）和全甲基化β-CD（TMB）。TMA·RALA·6H2O 和 TMB·RALA 的单晶 X 射线衍射显示，TMA 和 TMB 腔内 RALA 分子的取向显着不同，但在这两种情况下，客体分子均被各自的母体主体分子和残基完全封装。相邻复合单元的CD分子。虽然纯 RALA 在 46-48 °C 时熔化，但组合热分析技术表明，在加热各自的复合物时，RALA 的释放发生在显着更高的起始温度（150-170
• One-pot Synthesis of Permethylated α-CD-based Rotaxanes Having Alkylene Chain Axles and Their Structural Characteristics
  作者：Yosuke Akae、Takayuki Arai、Yasuhito Koyama、Hisashi Okamura、Kohei Johmoto、Hidehiro Uekusa、Shigeki Kuwata、Toshikazu Takata

  DOI：10.1246/cl.2012.806

  日期：2012.8.5

  Permethylated α-CD-based rotaxanes with short alkylene chains as an axle were synthesized through urea end-capping in one pot: Products were [2]rotaxane and [3]rotaxane. The head-to-head structure of [3]rotaxane obtained as a single isomer was confirmed by the characteristic 1H NMR peak shifts and X-ray single-crystal structure analysis.

  合取代的α-CD基旋转链合成了以短烷烃链作为轴的旋转链，通过在一个反应体系中进行脲端封闭。所得到的产物为[2]旋转链和[3]旋转链。获得的以头对头结构的[3]旋转链作为单一异构体，其特征在于1H NMR谱峰位移和X射线单晶结构分析进行了确认。
• Structural Analysis and Inclusion Mechanism of Native and Permethylated α-Cyclodextrin-Based Rotaxanes Containing Alkylene Axles
  作者：Yosuke Akae、Yasuhito Koyama、Hiromitsu Sogawa、Yoshihiro Hayashi、Susumu Kawauchi、Shigeki Kuwata、Toshikazu Takata

  DOI：10.1002/chem.201504882

  日期：2016.4.4

  The number of PMeCDs on the pseudorotaxane is flexible and mainly depends on the axle length. Peracetylated α‐CD (PAcCD)‐based rotaxanes are synthesized through O‐acetylation of the α‐CD‐based rotaxanes without any decomposition of the rotaxanated structures. The structures of PMeCD‐based [3]‐ and [4]rotaxanes, and the molecular dynamics calculations on [3]pseudorotaxanes, indicate that the tail face

  天然α-环糊精（α-CD）和全甲基化α-CD（PMeCD）的轮烷具有各种亚烷基短链作为轴，可以通过尿素封端法合成。天然α-CD倾向于形成[3]-或[5]假轮烷，而不是[2]-或[4]假轮烷，这表明偶联的CD充当单个片段。轴长为C18和C24的假轮烷的封端反应不会发生，因为轴末端被密集堆叠的CD覆盖。假轮烷上的PMeCD的数量是灵活的，并且主要取决于轴长。基于过乙酰化的α-CD（PAcCD）的轮烷是通过基于α-CD的轮烷的O-乙酰化而合成的，而轮烷的结构没有任何分解。基于PMeCD的[3]和[4]轮烷的结构，以及[3]假轮烷的分子动力学计算，表示PMeCD的尾面有规律地指向轮轴总站。根据获得的结果，可以得出结论，含有短亚烷基链的轮烷中CD的方向和数量取决于1）CD之间的相互作用，2）亚烷基轴的长度以及3）烷基之间的相互作用。 CD的轴端和尾端。
• Cyclodextrin-Based Ionic Liquids as Enantioselective Stationary Phases in Gas Chromatography
  作者：Nuno Costa、Sara Matos、Marco D. R. Gomes da Silva、M. Manuela A. Pereira

  DOI：10.1002/cplu.201300229

  日期：2013.12

  te ionic liquids were synthesized from the corresponding permethylated mono-6-hydroxycyclodextrins in a one-pot reaction and solvent-free procedure. Regioselective transformation of native α- and β-cyclodextrins with the use of a bulky tert-butyldiphenylsilyl protecting group afforded the desired 6-monosubstituted permethylated cyclodextrin derivatives in moderate yields. The new ionic liquids were

  合成了新的全甲基化的单-6-脱氧-6-吡啶-1-鎓和单-6-脱氧-6-（1-乙烯基-1H-咪唑-3-鎓）-α-和-β-环糊精三氟甲磺酸盐离子液体。一锅反应和无溶剂方法从相应的全甲基化的单-6-羟基环糊精中纯化得到。使用大的叔丁基二苯基甲硅烷基保护基对天然α-和β-环糊精进行区域选择性转化，以中等收率得到了所需的6-单取代的全甲基化的环糊精衍生物。在毛细管气相色谱柱中将新的离子液体作为固定相进行测试，以进行外消旋混合物的对映体-气相色谱分析中的手性鉴别。全甲基化的6-脱氧-6-吡啶-1-基-α-环糊精三氟甲磺酸盐显示出一些消旋酯和内酯以及环氧化物的良好对映异构体分离。
• Characterization of cyclomalto-hexaose and -heptaose derivatives by the reductive-cleavage method
  作者：Petra Mischnick-Lübbecke、Ralph Krebber

  DOI：10.1016/0008-6215(89)80003-5

  日期：1989.4

  The substitution patterns of cyclomalto-hexaose and -heptaose derivatives carrying alkyl, acyl, and carbamoyl substituents have been investigated by the reductive-cleavage method. The modified cyclomalto-hexaoses or -heptaoses were treated with triethylsilane and trimethylsilyl trifluoromethanesulfonate to give the corresponding 1,5- and 1,4-anhydroglucitol derivatives that were acetylated or, in the

  摘要：通过还原裂解方法研究了带有烷基，酰基和氨基甲酰基取代基的环麦芽六糖和庚糖衍生物的取代方式。用三乙基硅烷和三甲基甲硅烷基三氟甲磺酸酯处理改性的环麦芽六糖或庚二酮酶，得到相应的1,5-和1,4-脱水葡萄糖醇衍生物，将其乙酰化，或在乙酰基衍生物的情况下，将三氟乙酰基化，并通过glc-ms分析可以检测到烷基化化合物，烷基化不足或烷基化形成的微量产物或异构体组分。观察到酰氧基部分还原为烷氧基和酰基取代基的裂解。氨基甲酰基取代基在还原裂解的条件下是稳定的。