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

✍ Scribed by Emanuele Attolino; Giorgio Catelani; Felicia D'Andrea

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
184 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new stereocontrolled synthesis of b-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 b-D-galactopyranosides by an oxidation-reduction procedure; (b) a regiocontrolled formation of 4-deoxy-b-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-b-D-mannopyranosides and of an orthogonally protected b-D-mannopyranoside scaffold and, finally, by the transformation of lactose into the two biologically relevant disaccharides with primary structure b-D-Manp-(14)-D-Glc and b-D-ManNAcp-(14)-D-Glc.

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