Synthesis of beta-D-mannosides from beta-D-glucosides via an intramolecular SN2 reaction at C-2.
The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-trifyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.
Günther
W
W
Institut für Organische Chemie, Universität Mainz, Germany.
Kunz
H
H
D002240:Carbohydrate Sequence; D005960:Glucosides / Q000737:chemistry*; D006023:Glycoproteins / Q000737:chemistry; D007536:Isomerism; D008362:Mannosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data
D005960:Glucosides; D006023:Glycoproteins; D008362:Mannosides