40525-29-9

Usage

Chemical Classification

Aminosugar

Parent Structure

Hexopyranose (six-carbon sugar)

Functional Groups

Amino Group: Attached to the second carbon
Carboxyethyl Group: Attached to the third carbon
Deoxy Group: Replaces one hydroxyl group, located at the second carbon

Potential Applications

Medicinal Chemistry: Interest in drug synthesis
Biochemistry: Potential as a building block for modifying natural products

Upstream product

• 15454-37-2 2-amino-O³-((R)-1-carboxy-ethyl)-O⁶-phosphono-2-deoxy-D-glucose 
• 61633-75-8 N-acetyl-α-D-muramic acid 
• 31253-08-4 ethyl 2-iodopropionate 
• 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 
• 15892-26-9 benzyl 2-acetamido-3-O-<(R)-1-carboxyethyl>-2-deoxy-α-D-glucopyranoside 
• 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 

Relevant academic research and scientific papers

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.