502185-59-3

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 922520-78-3 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-talopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 502185-60-6 (2R,3S,6S)-3-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-6-methoxymethoxymethyl-3,6-dihydro-2H-pyran 

Relevant academic research and scientific papers

A new stereocontrolled access to β-D-mannopyranosides and 2-acetamido-2-deoxy-β-D-mannopyranosides starting from β-D-galactopyranosides

A new stereocontrolled synthesis of β-D-mannopyranosides was defined relying on a high yielding sequence based on the following three key steps: (a) a stereospecific inversion at C-2 of β-D-galactopyranosides by an oxidation-reduction procedure; (b) a regiocontrolled formation of 4-deoxy-β-D-threo-hex-3-enopyranosides; (c) a regio- and stereocontrolled hydroboration-oxidation of the above enol ethers. The flexibility of this new method was demonstrated by its extension to the synthesis of 2-acetamido-2-deoxy-β-D-mannopyranosides and of an orthogonally protected β-D-mannopyranoside scaffold and, finally, by the transformation of lactose into the two biologically relevant disaccharides with primary structure β-D-Manp-(1→4)-D-Glc and β-D-ManNAcp-(1→4)-D-Glc.