202343-12-2

Basic information

• Product Name: (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
• CAS NO: 202343-12-2
• Molecular Weight: 334.286
• Mol File: 202343-12-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid(202343-12-2)
• EPA Substance Registry System: (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid(202343-12-2)

Safety Data

• Hazardous Substances Data: 202343-12-2(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid" is a complex organic molecule with a tetrahydropyran ring and various functional groups, including acetylamino, azido, hydroxy, and carboxylic acid. It has a specific configuration of chiral centers, denoted by the R and S designations, and contains an acetylamino substituent at the 5-position as well as an azido group at the 2-position. The compound also features a tetrahydropyran-2-carboxylic acid moiety, which contributes to its overall structure and properties. (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid may have potential applications in medicinal chemistry, biochemistry, or organic synthesis, depending on its specific properties and reactivity.

Upstream product

• 189237-35-2 methyl [5-acetamido-3,5-dideoxy-2-azido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate 
• 3063-71-6 cytidine-5'-monophosphono-N-acetylneuraminic acid 

Relevant articles and documents

Synthesis and biological evaluation of non-hydrolyzable 1,2,3-triazole-linked sialic acid derivatives as neuraminidase inhibitors

αa-Sialic acid, azide 1 has been used as a substrate for the efficient preparation of 1,2,3-triazole derivatives of sialic acid using the copper-catalyzed azide-alkyne Huisgen cycloaddition ("click chemistry"). Our approach is to generate nonnatural N-glycosides of sialic acid, that are resistant to neuraminidase-catalyzed hydrolysis as opposed, to the natural Oglycosides. These N-glycosides would act as neuraminidase inhibitors to prevent the release of new virions. As a preliminary study, a small library of 1,2,3-triazole-linked sialic acid, derivatives has been synthesized in 71-89% yield. A. disaccharide mimic of sialic acid, has also been prepared using the α-sialic acid azide 1 and a C-8 propargyl sialic acid acceptor in 68 % yield. A model sialic acid coated dendrimer was also synthesized from a perpropargylated pentaerythritol acceptor. These novel sialic acid derivatives were then evaluated, as potential neuraminidase inhibitors using a 96-well plate fluorescence assay; micromolar IC50 values were observed, comparable to the known sialidase inhibitor Neu5Ac2en.