484-57-1

Upstream product

• 6619-04-1 N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 40642-89-5 2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 
• 166907-09-1 (2R,3S,4R,5R)-5-azido-6-(benzyloxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol 
• 80321-89-7 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-glucopyranose 
• 109819-63-8 β-Aethyl-2-desoxy-2-acetamino-4.6-benzyliden-D-glucopyranosid 
• 535-11-5 Ethyl 2-bromopropionate 
• 3804-93-1 (R)-2-[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-3a,5,6,6a-tetrahydro-furo[3,2-d]oxazol-6-yloxy]-propionic acid 

Relevant academic research and scientific papers

SYNTHETIC N-ACETYL-MURAMIC ACID DERIVATIVES AND USES THEREOF

The present invention provides N-acetyl-muramic acid (NAM) derivatives having Formula I, wherein Xa is selected from the group consisting of X1-X59, Ya is selected from the group consisting of H, monophosphate, uridine diphosphate and ethyl azide linker prepared from 2-azido-ethanol, and Za is selected from the group consisting of OH, an ethylene diamine coupled fluorophore, a peptide and a peptide with an ethylene diamine coupled fluorophore, wherein the peptide is selected from the group consisting of a monopeptide, a dipeptide, a tripeptide and a pentapeptide. Also provided are methods for synthesizing NAM derivatives and methods for modulating Nod2 in cells, modifying bacterial cell wall or modulating innate immune response by a subject to bacterial cells upon exposure to NAM derivatives.

A simple approach to the synthesis of muramic acid and isomuramic acid: 1H and 13C NMR characterisation

A simple and efficient synthesis of 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucose (muramic acid, 6) and its stereoisomer 2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose (isomuramic acid, 7) from methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (1) is described. Condensation of the O-3 oxyanion of 1 with an excess of methyl (R,S)-2-bromopropionate, followed by alkaline hydrolysis of the crude product and subsequent acidification, afforded crystalline methyl 2-acetamido-4,6-O-benzylidene-3-O-[(R,S)-1-carboxyethyl]-2-deo xy-α-D -glucopyranoside (2), in 72% yield, as a mixture of diastereomers. Esterification of 2 with an excess of diazomethane afforded quantitatively the corresponding mixture of epimeric esters, which were very easily separated by column chromatography on silica gel, giving pure (R) and (S) epimeric esters. Removal of the benzylidene and acetyl groups by acid hydrolysis gave, respectively, muramic acid (6), in 95% yield and isomuramic acid (7), in 93% yield. 1H and 13C NMR data are given.