123155-04-4

Basic information

• Product Name: Heptakis(2,3-di-O-Methyl-6-O-tert-butyldiMethylsilyl)-β-cyclodextrin
• Synonyms: Heptakis(2,3-di-O-Methyl-6-O-tert-butyldiMethylsilyl)-β-cyclodextrin;2,3-Di-O-Methyl-6-O-tert-butyldiMethylsilyl-β-cyclodextrin;6A,6B,6C,6D,6E,6F,6G-Heptakis-O-[(1,1-diMethylethyl)diMethylsilyl]-2A,2B,2C,2D,2E,2F,2G,3A,3B,3C,3D,3E,3F,3G-tetradeca-O-Methyl-β-cyclodextrin;Heptakis(2,3-di-O-Methyl-6-O-tert-butyldiMethylsilyl)cycloMaltoheptaose.;2,3-Dimethyl-6-tert-butyldimethylsilyl-b-cyclodextrin
• CAS NO: 123155-04-4
• Molecular Formula: C98H196O35Si7
• Molecular Weight: 2131.18234
• Product Categories: Intermediates & Fine Chemicals;Oligosaccharides;Pharmaceuticals;Oligosaccharides, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 123155-04-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: Heptakis(2,3-di-O-Methyl-6-O-tert-butyldiMethylsilyl)-β-cyclodextrin(CAS DataBase Reference)
• NIST Chemistry Reference: Heptakis(2,3-di-O-Methyl-6-O-tert-butyldiMethylsilyl)-β-cyclodextrin(123155-04-4)
• EPA Substance Registry System: Heptakis(2,3-di-O-Methyl-6-O-tert-butyldiMethylsilyl)-β-cyclodextrin(123155-04-4)

Safety Data

• Hazardous Substances Data: 123155-04-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A β-Cyclodextrin derivative.

Upstream product

• 123155-03-3 heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin 
• 74-88-4 methyl iodide 

Downstream Products

• 123155-05-5 heptakis(2,3-di-O-methyl)cyclomaltoheptaose 

Relevant articles and documents

Per-6-bromo-per-2,3-dimethyl-β-cyclodextrin

An efficient synthesis of the title compound, per-6-bromo-per-2,3-dimethyl-β-cyclodextrin, is described, giving access to a highly soluble cyclodextrin, which may be used for further chemical modification of β-cyclodextrin.Crystals of the target compound were grown and the solid state structure was determined by X-ray crystallography, revealing a cyclodextrin derivative whose conformation deviates substantially from C7 symmetry.

Micelles via self-assembly of amphiphilic beta-cyclodextrin block copolymers as drug carrier for cancer therapy

We developed intelligent, star-shaped amphiphilic β-cyclodextrin (β-CD) co-polymer nanocarriers to circumvent the poor drug loading and water-solubility of β-CD. The secondary hydroxyl groups of β-CD were methylated to improve solubility, and the primary hydroxyl groups were conjugated with mPEG-b-PCL-SH through disulfide linkage to amplify the hydrophobic cavity and enhance the stability of the nanocarrier. A series of amphiphilic β-CD block copolymers (CCPPs) differing in molecular weights were synthesized that could self-assemble into core-shell nanospheres measuring 50–70 nm in water. The different CCPP carriers were screened for their drug loading, encapsulation and release efficiencies, and CCPP-2 showed the highest drug loading capacity of 31.9% by weight. These nanocarriers accumulated at the tumor site through the EPR effect and released the drug in a controlled manner in the reductive tumor microenvironment, with negligible premature leakage and side effects. Therefore, CCPP-2 shows significant potential as a smart and efficient nanovehicle for anticancer drug delivery.

Amino acid derivatives of β-cyclodextrin

The syntheses of the heptaamino acid-substituted β-cyclodextrins per-6-[(phenylalanyl)amino]-β-cyclodextrin (6), per-6-cysteinyl-β-cyclodextrin (7), as well as the per-2,3-dimethyl-per-6-cysteinyl-β-cyclodextrin (12) are described. The amino acids were coupled to the primary face of the β-cyclodextrin torus using the backbone carboxylic acid functionality of phenylalanine and the side chain thiol group of cysteine. In the case of the heptacysteinyl derivatives, polyzwitterionic compounds were obtained and shown to be highly water soluble.