163860-80-8

Basic information

• Product Name: (2R,4S,5R,6R)-5-Acetylamino-4-azido-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• Synonyms: (2R,4S,5R,6R)-5-Acetylamino-4-azido-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS NO: 163860-80-8
• Molecular Weight: 716.697
• Mol File: 163860-80-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4S,5R,6R)-5-Acetylamino-4-azido-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S,5R,6R)-5-Acetylamino-4-azido-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(163860-80-8)
• EPA Substance Registry System: (2R,4S,5R,6R)-5-Acetylamino-4-azido-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(163860-80-8)

Safety Data

• Hazardous Substances Data: 163860-80-8(Hazardous Substances Data)

Upstream product

• 163860-78-4 methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-2-thio-D-glycero-α-D-galacto-nonulopyranosid)onate 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Relevant articles and documents

Structural and functional-group tuning in the design of neuraminidase inhibitors

Analogues of the disaccharide α-NeuAc-(2->6)-β-D-Gal-OR have been made by modifications at C-1 and C-6 of the galactose and at C-4 of the NeuAc unit, for structute-activity relationship studies with influenza virus neuraminidase.These studies indicate that for the influenza neuraminidase, a larger aglycon at C-1 of galactose is less preferred, whereas the restriction of the rotamer orientation at C-6 of galactose in the "tg" mode favors enzyme binding.Substitution at C-4 of the NeuAc unit has the most profound effect in the influenza neuraminidase hydrolysis and inhibition.For example, azido and acetamido groups at C-4 of the NeuAc units render the sialosides resistant to neuraminidase hydrolysis.However, these derivatives are not inhibitors of the neuraminidase, indicating their lack of binding.On the other hand, a 4-amino substitution of the NeuAc unit not only renders the corresponding sialosides neuraminidase-resistant, but also makes them potent neuraminidase inhibitors.This potent inhibition indicates that the 4-amino groups in these sialosides may engage in favorable interaction with amino acids at the neuraminidase active-site.The conclusion is also supported by docking studies of the carbohydrate structures at the neuraminidase active-site. Keywords: Neuraminidase inhibitors; Structure-activity relationship; Influenza virus neuraminidase