[1,2,3,4,5,6]O⁶-hexakis-(toluene-4-sulfonyl)-cyclo-lin-hexa[1α=>4]-D-glucopyranosyl | 21884-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1,2,3,4,5,6]O⁶-hexakis-(toluene-4-sulfonyl)-cyclo-lin-hexa[1α=>4]-D-glucopyranosyl
• 英文别名: [1,2,3,4,5,6]O⁶-Hexakis-(toluol-4-sulfonyl)-cyclo-lin-hexa[1α=>4]-D-glucopyranosyl；[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-31,32,33,34,35,36,37,38,39,40,41,42-dodecahydroxy-10,15,20,25,30-pentakis[(4-methylphenyl)sulfonyloxymethyl]-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]methyl 4-methylbenzenesulfonate
• CAS: 21884-25-3
• 化学式: C₇₈H₉₆O₄₂S₆
• 分子量: 1897.99
• InChiKey: MUKPVRFNLZRSBK-KWYFOIMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.73
• 重原子数：
  126.0
• 可旋转键数：
  24.0
• 环数：
  28.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  613.74
• 氢给体数：
  12.0
• 氢受体数：
  42.0

反应信息

• 作为反应物：
  描述：

  [1,2,3,4,5,6]O⁶-hexakis-(toluene-4-sulfonyl)-cyclo-lin-hexa[1α=>4]-D-glucopyranosyl 在 sodium hydroxide 作用下， 反应 48.0h， 以75%的产率得到per(3,6-anhydro)-α-cyclodextrin
  参考文献：
  名称：

  Per-3,6-anhydro-.alpha.-cyclodextrin and per-3,6-anhydro-.beta.-cyclodextrin

  摘要：

  The synthesis of the per-3,6-anhydro derivatives of alpha- and beta-cyclodextrins (CDs) is described starting from the corresponding per-6-tosylates. These could only be obtained as pure compounds following repeated HPLC under reversed-phase conditions of the crude products isolated after tosylation of alpha-CD and beta-CD in pyridine with p-toluenesulfonyl chloride. Treatment of the per-6-O-tosyl-alpha- and beta-CDs with warm aqueous sodium hydroxide solutions (50-60-degrees-C) afforded the per-3,6-anhydro-alpha- and beta-CDs in good yields. The development of an alternative and successful strategy for the synthesis of per-3,6-anhydro-alpha-CD from the known per-2,3-di-O-benzoyl-6-O-tosyl-alpha-CD relies upon the use of triethylamine as base in refluxing aqueous methanol. The per-3,6-anhydro-CDs have been fully characterized by FABMS and NMR spectroscopy. Their specific optical rotations, which are solvent dependent, confirm the chiral nature of these molecules. The anhydrides are soluble in such widely different solvents as dichloromethane and water. There is evidence from FABMS that per-3,6-anhydro-alpha-CD forms a complex with the triethylammonium cation while per-3,6-anhydro-beta-CD solubilizes nitrobenzene in deuterium oxide solutions.

  DOI：

  10.1021/jo00026a017
• 作为产物：
  描述：

  对甲苯磺酰氯 、 α-环糊精 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 [1,2,3,4,5,6]O⁶-hexakis-(toluene-4-sulfonyl)-cyclo-lin-hexa[1α=>4]-D-glucopyranosyl
  参考文献：
  名称：

  Polycationic Glycosides

  摘要：

  阳离子脂质早已被认为具有抗菌和抗真菌的作用。此前将阳离子脂质附着到碳水化合物基表面的研究表明，碳水化合物附着的阳离子脂质可能作为抗菌和抗真菌药物。为了理解这种可能性，我们合成了几系列与各种糖苷相连的阳离子脂质，旨在开发符合药物要求的抗微生物剂，特别是要求在非常低的浓度下有效，并且在被治疗的生物体内可降解。我们针对这一目标的初步结果已被呈现。

  DOI：

  10.3390/molecules16021508

文献信息

• Mimicking an antimicrobial peptidepolymyxin B by use of cyclodextrin
  作者：Hatsuo Yamamura、Ken Suzuki、Kazuma Uchibori、Atsushi Miyagawa、Masao Kawai、Chie Ohmizo、Takashi Katsu

  DOI：10.1039/c1cc16369h

  日期：——

  Cyclodextrin derivatives prepared to mimic a membrane active antibacterial peptide polymyxin B strongly permeabilized bacterial membrane and inhibited bacterial proliferation.

  环糊精衍生物可模拟膜活性抗菌肽多粘菌素 B，具有很强的渗透细菌膜和抑制细菌增殖的作用。
• Molecular Recognition by Self-Assembled Monolayers of Cyclodextrin on Ag
  作者：Hiroyuki Yamamoto、Yasushi Maeda、Hiromi Kitano

  DOI：10.1021/jp963916u

  日期：1997.8.1

  Self-assembled monolayer (SAM) of a thiolated cyclodextrin (CD) derivative was prepared, and stereoselective inclusional complexation of optically active azo dyes (p-or o-methyl red conjugates with chiral I-phenylethylamine, p-or o-MR-PEA) with both free CD and the SAM of the CD derivative on silver surface was investigated by using resonance Raman (RR) and surface-enhanced resonance Raman spectroscopy (SERRS), respectively. Characteristic molecular vibrations of functional groups of MR-PEA were used to describe the complexation. To our knowledge, this is the first report which compares the complexations of free and surface-confined CD by Raman spectroscopy. Association constants for the complexation (K) were determined from the relative intensity of Raman scattering of the dye complexed with CD. The K values for the complexation between MR-PEA and free CD determined by Raman spectroscopy were quite similar to those measured by W-visible spectroscopy, which confirmed the validity of Raman spectroscopy for the analysis of the inclusion phenomena. Though the K values of the SAM system were much larger than that of the free system, similar stereoselectivity was observed in both of the systems. The R enantiomer of o-MR-PEA was mon preferentially included both by free and surface-confined CD than the S-enantiomer, whereas a slight selectivity was observed for p-MR-PEA. The importance of the position of optically active carbon atom with respect to the azobenzene moiety, which penetrated into the cavity of CD, was suggested. Our findings show that the enantioselectivity of CD is preserved after immobilization onto solid surface.
• Selective preparation of hexakis (6-O-arenesulfonyl) -α-cyclodextrin
  作者：Fujita Kahee、Ohta Kazuko、Masunari Kozo、Obe Ken-ichi、Yamamura Hatsuo

  DOI：10.1016/s0040-4039(00)61134-6

  日期：1992.9
• Tosyl- und Mesyl-Derivate der Cyclodextrine (I)
  作者：W. Lautsch、R. Wiechert、H. Lehmann

  DOI：10.1007/bf01511661

  日期：1954.3