156297-61-9

Basic information

• Product Name: 6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octaazido-6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octadeoxy-γ-cyclodextrin
• Synonyms: 6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octaazido-6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octadeoxy-γ-cyclodextrin
• CAS NO: 156297-61-9
• Molecular Weight: 1497.24
• Mol File: 156297-61-9.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octaazido-6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octadeoxy-γ-cyclodextrin(CAS DataBase Reference)
• NIST Chemistry Reference: 6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octaazido-6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octadeoxy-γ-cyclodextrin(156297-61-9)
• EPA Substance Registry System: 6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octaazido-6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octadeoxy-γ-cyclodextrin(156297-61-9)

Safety Data

• Hazardous Substances Data: 156297-61-9(Hazardous Substances Data)

Upstream product

• 173094-60-5 octakis(6-chloro-6-deoxy)-γ-cyclodextrin 
• 168296-33-1 octakis(6-deoxy-6-iodo)-γ-cyclodextrin 
• 53784-84-2 octakis(6-bromo-6-deoxy)-γ-cyclodextrin 

Downstream Products

• 1608489-88-8 C₁₂₈H₁₆₀N₃₂O₃₂ 
• 1608489-90-2 C₁₂₈H₂₀₈N₃₂O₃₂ 
• 1608489-89-9 C₁₆₀H₂₂₄N₃₂O₃₂ 
• 171283-79-7 6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octaamino-6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octadeoxy-γ-cyclodextrin 

Relevant articles and documents

Efficient perfacial derivatization of cyclodextrins at the primary face

Synthesis of thirteen cyclodextrin (CD) derivatives via the per-6-bromo-6-deoxy-CD is reported in order to demonstrate the efficiency and ease of perfacial functionalization of α, β and γCD employing a Vilsmeier-Haack reagent.

Isothiocyanates and cyclic thiocarbamates of α,α'-trehalose, sucrose, and cyclomaltooligosaccharides

6,6'-dideoxy-6,6'-diisothiocyanato-α,α'-trehalose (4), 6-deoxy-6-isothiocyanato-α-D-fructofuranose β-D-fructopyranose 1,2':2,1'-dianhydride (11), 6,6'-dideoxy-6,6'-diisothiocyanatosucrose (16), and per(6-deoxy-6-isothiocyanato)-cyclomaltohexaose (23), -cyclomaltoheptaose (27), and -cyclomaltooctaose (31) have been prepared in high yield by reaction of the corresponding amino sugars with thiophosgene.In the absence of base, all isothiocyanates were stable and could be stored and acetylated without decomposition.In the presence of trietylamine, 6,6'-dideoxy-6,6'-diisothiocyanato-α,α'-trehalose underwent intramolecular cyclisation involving HO-4 to give the corresponding bis(cyclic thiocarbamate).The product of cyclisation at a single glucopyranosyl unit was obtained in the treatment of the above diisothiocyanate with mixed (H+, HO-) ion-exchange resin.Under identical reaction conditions, 6,6'-dideoxy-6,6'-diisothiocyanatosucrose yielded exclusively the product of intramolecular cyclisation at the D-glucopyranosyl moiety, while derivatives of α-D-fructofuranose β-D-fructopyranose 1,2':2,1'-dianhydride and cyclomaltooligosaccharides remained unchanged. Keywords: Sugar isothiocyanates; Trehalose; Difructose dianhydrides; Sucrose; Cyclomaltooligosaccharides

β-Cyclodextrin Covalent Organic Framework for Selective Molecular Adsorption

Covalent organic frameworks (COF) are complex functional systems constructed with atomic precision by linking well-defined building blocks through robust covalent bonds. β-cyclodextrin (β-CD) is a most employed supramolecule which bears a hydrophobic cavity guiding molecular specific recognitions. Building COF with asymmetric β-CD linkers is challenging and has never been reported. Here, β-CD COF is grown with heptakis(6-amino-6-deoxy)-β-CD and terephthalaldehyde in green solvents of water and ethanol at room temperature. The COF is characterized by powder X-ray diffraction, which matches well with the simulated crystal structure. Weaving β-CD into a framework through reticular chemistry allows the integration of a large amount of β-CD units (50 mol %), much higher than β-CD polymers. The β-CD COF has larger surface area, more uniform pore size, and higher thermal stability than the non-crystalline β-CD polymer produced by the same reagents. Finally, the β-CD COF holds abundant specific interaction sites enabling selective molecular adsorption.

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

A number of per-6-substituted cyclodextrin derivative syntheses have been effectively carried out in a planetary ball mill under solvent-free conditions. The preparation of Bridion and important per-6-amino/thiocyclodextrin intermediates without polar aprotic solvents, a source of byproducts and persistent impurities, could be performed. Isolation and purification processes could also be simplified. Considerably lower alkylthiol/halide ratio were necessary to reach the complete reaction in comparison with thiourea or azide reactions. While the presented mechanochemical syntheses were carried out on the millimolar scale, they are easily scalable.

Facial Synthesis and Bioevaluation of Well‐Defined OEGylated Betulinic Acid‐Cyclodextrin Conjugates for Inhibition of Influenza Infection

Betulinic acid (BA) and its derivatives exhibit a variety of biological activities, especially their anti‐HIV‐1 activity, but generally have only modest inhibitory potency against influenza virus. The entry of influenza virus into host cells can be competitively inhibited by multivalent derivatives targeting hemagglutinin. In this study, a series of hexa‐, hepta‐ and octavalent BA derivatives based on α-, β-and γ-cyclodextrin scaffolds, respectively, with varying lengths of flexible oligo(ethylene glycol) linkers was designed and synthesized using a microwave‐assisted copper‐catalyzed 1,3‐di-polar cycloaddition reaction. The generated BA‐cyclodextrin conjugates were tested for their in vitro activity against influenza A/WSN/33 (H1N1) virus and cytotoxicity. Among the tested com-pounds, 58, 80 and 82 showed slight cytotoxicity to Madin‐Darby canine kidney cells with viabilities ranging from 64 to 68% at a high concentration of 100 μM. Four conjugates 51 and 69–71 showed significant inhibitory effects on influenza infection with half maximal inhibitory concentration val-ues of 5.20, 9.82, 7.48 and 7.59 μM, respectively. The structure‐activity relationships of multivalent BA‐cyclodextrin conjugates were discussed, highlighting that multivalent BA derivatives may be potential antiviral agents against influenza infection.

Inhibition of influenza virus infection by multivalent pentacyclic triterpene-functionalized per-O-methylated cyclodextrin conjugates

Multivalent ligands that exhibit high binding affinity to influenza hemagglutinin (HA) trimer can block the interaction of HA with its sialic acid receptor. In this study, a series of multivalent pentacyclic triterpene-functionalized per-O-methylated cyclodextrin (CD) derivatives were designed and synthesized using 1, 3-dipolar cycloaddition click reaction. A cell-based assay showed that three compounds (25, 28 and 31) exhibited strong inhibitory activity against influenza A/WSN/33 (H1N1) virus. Compound 28 showed the most potent anti-influenza activity with IC50 of 4.7?μM. The time-of-addition assay indicated that compound 28 inhibited the entry of influenza virus into host cell. Further hemagglutination inhibition (HI) and surface plasmon resonance (SPR) assays indicated that compound 28 tightly bound to influenza HA protein with a dissociation constant (KD) of 4.0?μM. Our results demonstrated a strategy of using per-O-methylated β-CD as a scaffold for designing multivalent compounds to disrupt influenza HA protein-host receptor protein interaction and thus block influenza virus entry into host cells.