permethylated mono-6-hydroxy-β-cyclodextrin | 94789-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: permethylated mono-6-hydroxy-β-cyclodextrin
• 英文别名: 6-monohydroxy permethylated β-cyclodextrin；2^I−VII,3^I−VII,6^II−VII-icosa-O-methyl-β-cyclomaltoheptaose；2^I-VII,3^I-VII,6^II-VII-icosa-O-methyl-β-cyclomaltoheptaose；2^{I-VII_,3I-VII_,6II-VII}-eicosa-O-methyl-cyclomaltoheptaose；2^{I-VII_,3I-VII_,6I-VI}-eicosa-O-methylcyclomaltoheptaose；(2,3-di-O-methyl)hexakis(2,3,6-tri-O-methyl)cyclomaltoheptaose；6-O-monohydroxy permethylated β-cyclodextrin
• CAS: 94789-61-4
• 化学式: C₆₂H₁₁₀O₃₅
• 分子量: 1415.53
• InChiKey: FUPKESVQJIGDBJ-LGVGIWCKSA-N

物化性质

• 沸点：
  1113.9±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.15
• 重原子数：
  97.0
• 可旋转键数：
  27.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  334.05
• 氢给体数：
  1.0
• 氢受体数：
  35.0

反应信息

• 作为反应物：
  描述：

  permethylated mono-6-hydroxy-β-cyclodextrin 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 作用下， 生成 5^A-carboxy-5^A-dehydroxymethyl-2^A,2^B,2^C,2^D,2^E,2^F,2^G,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^B,6^C,6^D,6^E,6^F,6^G-icosa-O-methyl-β-cyclodextrin
  参考文献：
  名称：

  Selective access and full characterization of mono-acidic permethylated β-cyclodextrin derivatives and their methyl esters

  摘要：

  Three acidic derivatives of permethylated beta-cyclodextrin, 2(I)-O-carboxymethyl-2(II-VII),3(I-VII),6(I-VII)-eicosa-O-methyl-cyclomaltoheptaose, 6(I)-O-carboxymethyl-2(I-VII),3(I-VII),6(II-VII)-eicosa-O-methyl-cyclomaltoheptaose, 6(I)-desoxy-6(I)-carboxy-2(I-VII),3(I-III),6(II-VII)-eicosa-O-methyl-cyclomaltoheptaose and the corresponding methyl esters have been synthesized with good yields starting from mono-hydroxy permethylated beta-CD prepared via tert-butyldimethylsilyl protection in 6-position and p-methoxybenzyl protection at the 2-position. All of these compounds were fully characterized by high field H-1 and C-13 NMR and HPLC/MS. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00446-4
• 作为产物：
  描述：

  [(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecamethoxy-5,15,20,25,30,35-hexakis(methoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-10-yl]methyl 4-methylbenzenesulfonate 在 萘 、 sodium 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到permethylated mono-6-hydroxy-β-cyclodextrin
  参考文献：
  名称：

  多功能 6-O-单糖基和 6-单羟基全​​甲基化 α-、β- 和 γ-环糊精的新大规模制备

  摘要：

  描述了用于制备通用 6-O-单糖基和 6-单羟基全​​甲基化 α-、β-和 γ-环糊精的新实用方法。

  DOI：

  10.1246/cl.2002.514

文献信息

• Amphiphilic cyclodextrin derivatives, method for preparation thereof and uses thereof
  申请人：Perly Bruno

  公开号：US20070142324A1

  公开（公告）日：2007-06-21

  The invention relates to cyclodextrin derivatives of formula (I): in which: R 1 ═—NH-E-AA-(L 1 ) p (L 2 ) q where E=a linear or branched Cl-Cl 5 hydrocarbon-based group with, optionally, one or more hetero atoms; AA=the residue of an amino acid; L 1 and L 2 =a C 6 -C 24 hydrocarbon-based group with, optionally, one or more hetero atoms; p and q=0 or 1, at least one being ≠0; R 2 ═H, —CH 3 , isopropyl, hydroxypropyl, sulphobutyl ether; R 3 ═H or R 2 , except when R 2 =hydroxypropyl; all the R 4 ═—OH or R 2 , except when R 2 =hydroxypropyl, or at least one of the R 4 ═R 1 ; n=5, 6 or 7. The invention also relates to a process for preparing them, and to inclusion complexes and organized surfactant systems comprising them.

  该发明涉及以下式（I）的环糊精衍生物： 其中： R 1 ═—NH-E-AA-(L 1 ) p (L 2 ) q 其中E=线性或支链的Cl-Cl 5 碳氢基团，可选地，含有一个或多个杂原子；AA=氨基酸的残基；L 1 和L 2 =含有一个或多个杂原子的C 6 -C 24 碳氢基团；p和q=0或1，至少一个不等于0； R 2 ═H，—CH 3 ，异丙基，羟丙基，磺丁基醚； R 3 ═H或R 2 ，除非R 2 =羟丙基； 所有的R 4 ═—OH或R 2 ，除非R 2 =羟丙基，或者至少一个R 4 ═R 1 ；n=5、6或7。该发明还涉及一种制备它们的方法，以及包含它们的包合物和有序表面活性剂系统。
• Preparation and Photodynamic Activities of Silicon(IV) Phthalocyanines Substituted with Permethylated β-Cyclodextrins
  作者：Janet T. F. Lau、Pui-Chi Lo、Wing-Ping Fong、Dennis K. P. Ng

  DOI：10.1002/chem.201100621

  日期：2011.6.27

  A series of silicon(IV) phthalocyanines linked to two permethylated β‐cyclodextrin moieties through different spacers at the axial positions have been synthesized and characterized. The effects of these spacers on the photophysical properties and in vitro photodynamic activities have also been examined. Having two bulky hydrophilic substituents, all of these compounds are soluble and essentially nonaggregated

  合成并表征了一系列通过两个不同间隔基与两个全甲基化β-环糊精部分连接的硅（IV）酞菁。还检查了这些间隔物对光物理性质和体外光动力活性的影响。具有两个庞大的亲水性取代基，所有这些化合物都可溶于DMF，甚至在水性介质中且基本上不聚集。对于类似物而言，DMF中的荧光和单态氧量子产率较低，间隔基中的氨基与酞菁环之间的间隔最短。该化合物的荧光量子产率在水中可能由于氨基的质子化而增加，这抑制了还原淬灭过程。50个值在0.04-1.32μ的范围中号。具有α，ω-氨基羟基戊基接头的类似物显示出最高的效价，这可以归因于其高细胞摄取和高效产生细胞内活性氧的能力。该化合物还在溶酶体中显示优先定位，主要通过凋亡诱导细胞死亡，并在体内抑制肿瘤的生长。结果表明，它是用于光动力疗法的有前途的光敏剂。
• Communication: A Convenient Synthesis of Per-<i>O</i>-Methylated 6-<i>O</i>-Monosubstituted ß-Cyclodextrins
  作者：Niculina Lupescu、Catherine K. Y. Ho、Guochen Jia、Jiri J. Krepinsky

  DOI：10.1080/07328309908543982

  日期：1999.1.1

  Cyclodextrins are cyclic oligosaccharides that function as chiral host molecules exhibiting enantioselectivity in reactions with racemic guests1 and thus they represent a significant moiety of artificial enzymes.2 The most easily obtainable and relatively inexpensive are s-cyclodextrins (s-CD), cyclic heptaglucosides in which glucopyranosyl residues are linked by an α(1-4) glycosidic bonds. s-CD is

  环糊精是环状低聚糖，起手性宿主分子的作用，在与外消旋客体的反应中表现出对映选择性1，因此它们代表了人工酶的重要组成部分。2最容易获得且相对便宜的是s-环糊精（s-CD），环状七葡糖苷。吡喃葡萄糖基残基通过α（1-4）糖苷键连接。令人惊讶的是，s-CD在水中的溶解度很差（100毫升中为1.8克）3，但其衍生物的溶解度通常要好得多。例如，所有仲羟基都被甲基化的s-CD在室温下会形成50％的水溶液4，甚至完全甲基化的s-CD在水中的溶解度（100毫升中为17 g）5是s-CD本身的十倍。甲基化还会改变底物与s-CD的结合，从而经常增加其特异性和强度，6和使羟基不反应。因此，令人感兴趣的是制备其中酶模拟基团与一个羟基（...
• Substrate structure governs maximum rate of catalysis exerted by cyclodextrin oxidase chemzymes
  作者：Jeannette Bjerre、Mikael Bols

  DOI：10.1007/s10847-010-9774-8

  日期：2011.4

  highly important factor governing how effectively the oxidation reaction can be catalyzed. Amino acid-type substrates were not prone to catalysis, which yields new information about the limits of CD catalysis. Aniline showed some non-quantifiable catalysis, but for quinones and benzyl alcohols no net catalysis was detected. For aminophenol oxidation, o-aminophenols are far better substrates than p-aminophenols

  选择性修饰的 α- 和 β- 环糊精酮或醛在各种小的亲脂性底物上充当人工氧化酶。底物的结构是决定氧化反应催化效率的非常重要的因素。氨基酸型底物不易被催化，这产生了关于 CD 催化极限的新信息。苯胺显示出一些不可量化的催化作用，但对于醌和苯甲醇，未检测到净催化作用。对于氨基苯酚氧化，邻氨基苯酚是比对氨基苯酚更好的底物。CD 催化的反应遵循 Michaelis-Menten 动力学，涉及底物的 CD 腔结合和底物识别，因此包含许多天然酶催化的标志。共氧化剂 H2O2 与 CD 催化羰基的强结合是底物随后氧化的先决条件，因此， 与 β-CD 二醛的结合显示出很强的结合力（Kd = 1.4 mM）。β-CD 6A,6D-二酮与 的结合比醛弱，因此是一种效率较低的氧化酶。适用于 CD 化学酶催化的广泛底物为合成生物学的未来范围带来了乐观。
• Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin
  作者：Jun Terao、Yohei Konoshima、Akitoshi Matono、Hiroshi Masai、Tetsuaki Fujihara、Yasushi Tsuji

  DOI：10.3762/bjoc.10.297

  日期：——

  We synthesized symmetrically insulated oligo(para-phenylene) and oligothiophene with a pseudo-linked [3]rotaxane structure by full rotation of glucopyranose units via a flipping (tumbling) mechanism in the π-conjugated guest having two permethylated β-cyclodextrin units at both ends. We also succeeded in the synthesis of an organic-soluble fixed [3]rotaxane by a cross-coupling or complexation reaction of thus formed pseudo linked [3]rotaxane. Oligo(para-phenylene), oligothiophene, and porphyrin derivatives were used as π-conjugated guests with stopper groups.

  我们通过在π共轭客体中具有两个双甲基化β-环糊精单元的两端全旋转葡萄糖吡喃单元的翻转（翻滚）机制，合成了具有伪链接[3]轮烷结构的对称绝缘寡聚（对）苯和寡噻吩。我们还通过交叉偶联或络合反应成功合成了有机溶剂可溶的固定[3]轮烷。寡（对）苯、寡噻吩和卟啉衍生物被用作带有停滞基团的π共轭客体。