heptakis(2,3-di-O-acetyl-6-bromo-6-deoxy)-β-cyclodextrin | 53784-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis(2,3-di-O-acetyl-6-bromo-6-deoxy)-β-cyclodextrin
• 英文别名: heptakis(2,3-di-O-acetyl-6-bromo-6-deoxy)cyclomaltoheptaose
• CAS: 53784-86-4
• 化学式: C₇₀H₉₁Br₇O₄₂
• 分子量: 2163.8
• InChiKey: OKHPACFLCITJEG-DCBUKTJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  119.0
• 可旋转键数：
  21.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  497.42
• 氢给体数：
  0.0
• 氢受体数：
  42.0

反应信息

• 作为反应物：
  描述：

  N-丁基咪唑 、 heptakis(2,3-di-O-acetyl-6-bromo-6-deoxy)-β-cyclodextrin 以 N,N-二甲基甲酰胺 为溶剂， 生成 heptakis[2,3-di-O-acetyl-6-(1-n-butyl-1H-imidazol-2-yl)-6-deoxy]-β-cyclodextrin
  参考文献：
  名称：

  Cell transfection with polycationic cyclodextrin vectors

  摘要：

  Polycationic cyclodextrins (CDs) were complexed with plasmid DNA and their effectiveness as vectors was tested on COS-7 cells. These CDs were modified with pyridylamino, alkylimidazole, methoxyethylamino or primary amine groups at 6-positions of the glucose units. Uncharged CDs, beta-CD, hydroxypropyl-beta-CD, and dimethyl-beta-CD were also tested, but these did not form stable complexes with the DNA and produced only a slight improvement in transfection level over DNA alone. The polycationic CDs neutralised DNA to form stable nanoparticulate complexes. The transfection efficiency of these CDs was dependent on the substituents present, with the most efficient having either an amino, pyridylamino or butylimidazole group at the 6-positions and unmodified 2- and 3-hydroxyls. One of the most effective vectors, heptakispyridylamino CD, produced a 4000-fold increase in transfection level over DNA alone. Levels were improved 10-fold by use of the endosomolytic agent, chloroquine. The transfection efficiency of the best of these systems in serum equals that of DOTAP in serum. Studies with P-32-labelled plasmid DNA indicate that the polycationic CDs are exceptional promoters of DNA cellular-uptake, the most efficient surpassing DOTAP. Uptake is dependent on proteoglycan-mediated binding to cells. The data imply that intracellular trafficking but not cellular uptake, may be the rate-limiting step in the transfection process. These initial results indicate that CDs are useful templates for further modification to produce molecular constructs capable of enhanced gene delivery. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2004.01.001
• 作为产物：
  描述：

  heptakis(2,3-di-O-acetyl-6-O-methylsulfonyl)cyclomaltoheptaose 在 sodium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以82%的产率得到heptakis(2,3-di-O-acetyl-6-bromo-6-deoxy)-β-cyclodextrin
  参考文献：
  名称：

  通过叔丁基二甲基硅烷化对环麦芽寡糖的选择性化学修饰

  摘要：

  摘要在咪唑存在下，在N，N-二甲基甲酰胺中将环麦芽庚糖和环麦芽八糖与叔丁基氯二甲基硅烷选择性反应，得到七（6-O-叔丁基二甲基甲硅烷基）（21）和八（6-O-叔丁基二甲基甲硅烷基）。 （27）的衍生物的收率分别为70％和67％。环麦芽寡糖的十二个部分甲基化的区域异构体，即六（2-和3-O-甲基，以及2,6-和3,6-二-O-甲基）环麦芽六糖，七（2-，3-和-） 6-O-甲基和2,3-，2,6-和3,6-二-O-甲基）环麦芽糖酶和八（6-O-甲基和2,3-二-O-甲基）环麦芽糖酶，分别通过六（6-O-叔丁基二甲基甲硅烷基）环麦芽六糖（2），21和27作为关键中间体，通过明确的路线制备了晶体。

  DOI：

  10.1016/0008-6215(89)80004-7

文献信息

• A Novel Protocol for the Regioselective Bromination of Primary Alcohols in Unprotected Carbohydrates or Glycosides
  作者：Weihua Xue、Lifen Zhang

  DOI：10.1002/cjoc.201200211

  日期：2012.7

  The regioselective and efficient bromination of primary hydroxyl groups in unprotected carbohydrates or glycosides is successfully achieved by using (chloro‐phenylthio‐methylene)dimethylammoniumchloride (CPMA) in the presence of tetrabutylammonium bromide (TBAB) in dry DMF.

  在干燥的DMF中，在四丁基溴化铵（TBAB）存在下，使用（氯-苯硫基-亚甲基）二甲基氯化铵（CPMA）成功地实现了未保护的碳水化合物或糖苷中伯羟基的区域选择性和有效溴化。
• Complexation of Inorganic Anions with Heptakis(6-butylamino-6-deoxy)-<i>β</i>-cyclodextrin and Its Analogs in Acidic Media
  作者：Yoshihisa Matsui、Eiji Tanemura、Tohoru Nonomura

  DOI：10.1246/bcsj.66.2827

  日期：1993.10

  Heptakis(6-butylamino-6-deoxy)-β-cyclodextrin (2) forms 1 : 1 complexes with several inorganic anions in 0.10 mol dm−3 HCl or DCl at 25 °C. The binding constant for a complex of 2 with the SO42− ion was remarkably larger than those for complexes of 2 with univalent anions and those for complexes of the α- (1) and γ-cyclodextrin (3) analogs with the SO42− ion. The circular arrangement of the protonated amino groups in

  Heptakis(6-丁基氨基-6-deoxy)-β-环糊精 (2) 在 25 °C 下在 0.10 mol dm-3 HCl 或 DCl 中与几种无机阴离子形成 1:1 复合物。2 与 SO42- 离子的复合物的结合常数明显大于 2 与单价阴离子的复合物以及 α- (1) 和 γ-环糊精 (3) 类似物与 SO42- 离子的复合物的结合常数。2中质子化氨基的环状排列可能有利于与二价阴离子的静电相互作用。