6533b834fe1ef96bd129cc1c
RESEARCH PRODUCT
Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2
Horst KunzWolfgang Günthersubject
chemistry.chemical_classificationMannosidesIntramolecular reactionStereochemistryMolecular Sequence DataOrganic ChemistryLeaving groupGeneral MedicineBiochemistryAnalytical ChemistryCarbohydrate SequenceGlucosidesIsomerismAldosechemistryMannosidesIntramolecular forceNucleophilic substitutionSN2 reactionProtecting groupGlycoproteinsdescription
Abstract The selective synthesis of β- d -mannosides was achieved by first synthesizing β- d -glucosides that carry a N -phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding β- d -mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O -triflyl 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 β d -mannoside.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1992-04-10 | Carbohydrate Research |