2^A,2^B,2^C,2^D,2^E,2^F,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^A,6^B,6^C,6^D,6^E,6^F,6^G-eicosa-O-methylcyclomaltoheptaose | 153313-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2^A,2^B,2^C,2^D,2^E,2^F,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^A,6^B,6^C,6^D,6^E,6^F,6^G-eicosa-O-methylcyclomaltoheptaose
• 英文别名: 2^{I-VI_,3I-VII_,6I-VII}-eicosa-O-methyl-cyclomaltoheptaose；2^{I-VI_,3I-VII_,6I-VII}-eicosa-O-methylcyclomaltoheptaose；2(A)-O-hydroxy-per-O-methyl-β-cyclodextrin；2A-hydroxy-per-O-methyl-β-cyclodextrin；eicosa-O-methyl-β-cyclodextrin；(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36R,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,38,39,40,41,42,43,44,45,46,47,48,49-tridecamethoxy-5,10,15,20,25,30,35-heptakis(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-37-ol
• CAS: 153313-11-2
• 化学式: C₆₂H₁₁₀O₃₅
• 分子量: 1415.53
• InChiKey: XXXZAPNZTGYXER-KCZGSDITSA-N

物化性质

• 沸点：
  1124.6±65.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  97
• 可旋转键数：
  27
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  334
• 氢给体数：
  1
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  异氰酸正丁酯 、 2^A,2^B,2^C,2^D,2^E,2^F,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^A,6^B,6^C,6^D,6^E,6^F,6^G-eicosa-O-methylcyclomaltoheptaose 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以31%的产率得到2^A-O-(N-butylamino)carbonyl-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^A,6^B,6^C,6^D,6^E,6^F,6^G-eicosa-O-methylcyclomaltoheptaose
  参考文献：
  名称：

  Facile preparation of mono-2-O-modified eicosa-O-methylcyclomaltoheptaoses (-β-cyclodextrins)

  摘要：

  Mono-2-O-benzylated eicosa-O-methylcyclomaltoheptaose (-beta-cyclodextrin) was prepared in one pot from cyclomaltoheptaose (beta-cyclodextrin) in 33% isolated yield and quantitatively converted to mono-2-OH-free eicosa-O-methylcyclomaltoheptaose, which is the key compound for further modification. Transformation of this 2-OH group successfully gave several mono-2-O-modified eicosa-O-methylcyclomaltoheptaoses such as the acetate, the N,N-dimethylcarbamate, the N-n-butylcarbamate, the methanesulfonate, and the S-methyidithiocarbonate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00315-4
• 作为产物：
  描述：

  2^A-O-benzyl-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^A,6^B,6^C,6^D,6^E,6^F,6^G-eicosa-O-methylcyclomaltoheptaose 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以96%的产率得到2^A,2^B,2^C,2^D,2^E,2^F,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^A,6^B,6^C,6^D,6^E,6^F,6^G-eicosa-O-methylcyclomaltoheptaose
  参考文献：
  名称：

  二异丁基氢化铝 (DIBAL-H) 促进全甲基化 β-环糊精的二级边缘区域选择性去甲基化：机械建议

  摘要：

  二异丁基氢化铝 (DIBAL-H) 可促进全甲基化 P-环糊精的 2 A - 和 3 B - 位的二级边缘区域选择性双-脱-O-甲基化。该结果与全苄基化环糊精的选择性双-脱-O-苄基化形成对比，其中区域选择性脱保护发生在初级边缘。为了深入了解这种显着对比行为的机制，合成了两种相应的在 2 位或 3 位具有醇功能的全甲基化环糊精。3-位醇的环糊精与DIBAL-H反应得到2A，3B-二醇，而2-位醇的环糊精不反应。这一观察结果使我们能够提出一种去甲基化反应的机制，该机制涉及每个去甲基化步骤两分子铝试剂，与之前关于脱苄反应的假设一致。第二个去甲基化步骤似乎比第一个更快，铝的配位现在是一个分子内过程。

  DOI：

  10.1002/ejoc.200901230

文献信息

• Synthesis of two mono-deoxy β-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism
  作者：Su Long Xiao、De Min Zhou、Ming Yang、Fei Yu、Li He Zhang、Pierre Sinaÿ、Yong Min Zhang

  DOI：10.1016/j.cclet.2012.10.023

  日期：2012.12

  Diisobutylaluminium hydride (DIBAL-H) promotes secondary rim regioselective bis-de-O-methylation of permethylated β-cyclodextrin (β-CD) to give diol 2. To gain an insight into the mechanism of this remarkable regioselective behavior, two corresponding permethylated β-CDs with an alcohol function at either 2- or 3-position were synthesized in our previous study. As a step further to this work, the two

  二异丁基氢化铝（DIBAL-H）促进仲轮缘区域选择性双-脱Ö全甲基化的-methylation β环糊精（β -CD），得到二醇2。为了深入了解这种显着的区域选择性行为的机理，我们在先前的研究中合成了两个相应的在2位或3位具有醇功能的全甲基化β- CD。作为这项工作的进一步步骤，在2,2'-偶氮二异丁腈的存在下，将两种化合物与氢化三丁基锡进行脱氧反应，得到相应的2-和3-脱氧过甲基化的β -CD衍生物（19和16）。这两种化合物的结构通过1D和2D NMR和HRMS表征。化合物16和19不能与DIBAL-H反应，这表明O -2 A和O -3 B对于DIBAL-H促进的全甲基化β -CD的双-脱-O-甲基化反应是必需的。
• Synthesis of Cyclodextrins with Carboxylic Acids at the Secondary Rim and an Evaluation of Their Properties as Chemzymes for Glycoside Hydrolysis
  作者：You Zhou、Emil Lindbäck、Lavinia G. Marinescu、Christian Marcus Pedersen、Mikael Bols

  DOI：10.1002/ejoc.201200404

  日期：2012.7

  Seven β-cyclodextrin-mono-, -di- or -tetra-O-acetic acids were prepared and investigated for their propertiesas catalysts of the hydrolysis of four nitrophenyl glycosides.

  制备了七种β-环糊精-单-、-二-或-四-O-乙酸，并研究了它们作为四种硝基苯基糖苷水解催化剂的性质。
• Synthesis, NMR Spectroscopic Characterization and Polysiloxane-Based Immobilization of the Three Regioisomeric Monooctenylpermethyl-β-cyclodextrins and Their Application in Enantioselective GC
  作者：H. Cousin、O. Trapp、V. Peulon-Agasse、X. Pannecoucke、L. Banspach、G. Trapp、Z. Jiang、J. C. Combret、V. Schurig

  DOI：10.1002/ejoc.200300108

  日期：2003.9

  Each of the regioisomeric mono-oct-7-enylated permethylated β-cyclodextrin derivatives was anchored by hydrosilylation to a hydridomethyldimethylsiloxane copolymer to yield unambiguously O-2-, O-3-, and O-6-bonded chiral stationary phases (CSP) of Chirasil-Dex, which were evaluated in enantioselective gas chromatography (GC). O-6-Chirasil-Dex displayed slightly inferior enantioselectivity relative to

  2I-VI,3I-VII,6I-VII-Eicosa-O-methyl-2I-O-(oct-7-enyl)cyclomaltogeptaose, 2I-VII,3I-VI,6I-VII-eicosa-O-methyl-3I -O-(oct-7-enyl) cyclomaltogeptaose 和 2I-VII,3I-VII,6I-VI-eicosa-O-methyl-6I-O-(oct-7-enyl) cyclomaltoheptaose 通过选择性引入在选择性甲基化的环麦芽七糖（β-环糊精，CD）的 O-2、O-3 或 O-6 位之一的辛-7-烯基，并且根据合成路线，通过随后的全甲基化步骤。每个区域异构的单 oct-7-enylated 全甲基化 β-环糊精衍生物都通过氢化硅烷化锚定到氢化甲基二甲基硅氧烷共聚物上，以产生明确的 O-2-、O-3- 和 O-6-键合的手性固定相 (CSP)
• Selective access and full characterization of mono-acidic permethylated β-cyclodextrin derivatives and their methyl esters
  作者：S. Tisse、V. Peulon-Agasse、H. Oulyadi、F. Marsais、J.C. Combret

  DOI：10.1016/s0957-4166(03)00446-4

  日期：2003.8

  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.
• Regioselective synthesis of methylated β-cyclodextrins leaving hydroxy groups
  作者：Koji Matsuoka、Yoko Shiraishi、Daiyo Terunuma、Hiroyoshi Kuzuhara

  DOI：10.1016/s0040-4039(00)02276-0

  日期：2001.2

  A series of methylated beta -cyclodextrins (CDs) regioselectively leaving one or two hydroxy groups were prepared, and fluorescence spectroscopic measurements showed that they have unique binding characteristics against 2-p-toluidinylnaphthalene-6-sulfonate as a guest molecule in aqueous solution. (C) 2001 Elsevier Science Ltd. All rights reserved.