33012-49-6

Basic information

• Product Name: HEPTA-O-ACETYL-SS-MALTOSYL AZIDE
• Synonyms: HEPTA-O-ACETYL-SS-MALTOSYL AZIDE;2,3,6,2',3',6'-Hepta-O-acetyl-b-maltosyl azide;2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl azide;2,3,6,2',3',4',6'-Hepta-O-acetyl-b-maltosyl azide
• CAS NO: 33012-49-6
• Molecular Formula: C₂₆H₃₅N₃O₁₇
• Molecular Weight: 661.567
• Mol File: 33012-49-6.mol
• Article Data: 21

Chemical Properties

• Melting Point: 181-183 °C
• Appearance: /
• CAS DataBase Reference: HEPTA-O-ACETYL-SS-MALTOSYL AZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: HEPTA-O-ACETYL-SS-MALTOSYL AZIDE(33012-49-6)
• EPA Substance Registry System: HEPTA-O-ACETYL-SS-MALTOSYL AZIDE(33012-49-6)

Safety Data

• Hazardous Substances Data: 33012-49-6(Hazardous Substances Data)

Upstream product

• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 
• 60-29-7 diethyl ether 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 68682-05-3 2,2',3,3',4',6,6'-hepta-O-acetyl-β-D-maltosyl bromide 
• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 

Downstream Products

• 1351017-43-0 C₃₇H₆₂N₂O₁₂ 
• 1351017-40-7 C₅₁H₇₆N₂O₁₉ 
• 1338457-74-1 5-[p-(aminosulfonyl)phenyl]-1-(hepta-O-acetyl-β-D-maltopyranosyl)-1H-1,2,3-triazole 
• 1017276-55-9 4-[4-(aminosulfonyl)phenyl]-1-(hepta-O-acetyl-β-D-maltopyranosyl)-1H-1,2,3-triazole 
• 77489-36-2 2,3,6-tri-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl]-β-D-glucopyranosyl isothiocyanate 

Relevant articles and documents

Glucose and Maltose Surface-Functionalized Thermoresponsive Poly(N-Vinylcaprolactam) Nanogels

Soft nanoparticles are interesting materials due to their size, deformability, and ability to host guest molecules. Surface properties play an essential role in determining the fate of the particles in biological medium, and coating of the nanoparticles (and polymers) with carbohydrates has been found to be an efficient strategy for increasing their biocompatibility and fine-tuning other important properties such as aqueous solubility. In this work, soft nanogels of poly(N-vinylcaprolactam), PNVCL, were surface-functionalized with different glucose and maltose ligands, and the colloidal properties of the gels were analyzed. The PNVCL nanogels were first prepared via semibatch precipitation polymerization, where a comonomer, propargyl acrylate (PA), was added after preparticle formation. The aim was to synthesize "clickable" nanogels with alkyne groups on their surfaces. The nanogels were then functionalized with two separate azido-glucosides and azido-maltosides (containing different linkers) through a copper-catalyzed azide-alkyne cycloaddition (CuAAc) click reaction. The glucose and maltose bearing nanogels were thermoresponsive and shrank upon heating. Compared to the PNVCL-PA nanogel, the carbohydrate bearing ones were larger, more hydrophilic, had volume phase transitions at higher temperatures, and were more stable against salt-induced precipitation. In addition to investigating the colloidal properties of the nanogels, the carbohydrate recognition was addressed by studying the interactions with a model lectin, concanavalin A (Con A). The binding efficiency was not affected by the temperature, which indicates that the carbohydrate moieties are located on the gel surfaces, and are capable of interacting with other biomolecules independent of temperature. Thus, the synthesis produces nanogels, which have surface functions capable of biorelevant interactions and a thermoresponsive structure. These types of particles can be used for drug delivery.

Design, synthesis of oleanolic acid-saccharide conjugates using click chemistry methodology and study of their anti-influenza activity

The development of entry inhibitors is an emerging approach to the inhibition of influenza virus. In our previous research, oleanolic acid (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor. Herein, as a further study, we report the preparation of a series of OA-saccharide conjugates via the CuAAC reaction, and the anti-influenza activity of these compounds was evaluated in vitro. Among them, compound 11b, an OA-glucose conjugate, showed a significantly increased anti-influenza activity with an IC50 of 5.47 μM, and no obvious cytotoxic effect on MDCK cells was observed at 100 μM. Hemagglutination inhibition assay and docking experiment indicated that 11b might interfere with influenza virus infection by acting on HA protein. Broad-spectrum anti-influenza experiments showed 11b to be robustly potent against 5 different strains, including influenza A and B viruses, with IC50 values at the low-micromole level. Overall, this finding further extends the utility of OA-saccharide conjugates in anti-influenza virus drug design.

Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water

Transition-metal-catalyzed or metal-free azide-alkyne cycloadditions are methods to access 1,4- or 1,5-disubstituted 1,2,3-triazoles. Although the copper-catalyzed cycloaddition to access 1,4-disubstituted products has been applied to biomolecular reaction systems, the azide-alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition.