502185-59-3Relevant articles and documents
A new stereocontrolled access to β-D-mannopyranosides and 2-acetamido-2-deoxy-β-D-mannopyranosides starting from β-D-galactopyranosides
Attolino, Emanuele,Catelani, Giorgio,D'Andrea, Felicia
, p. 8815 - 8818 (2007/10/03)
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.