Epoxidation of C-branched glycals: unexpected stereochemical results and their theoretical rationale.
This paper describes the synthesis of C-3 methyl-branched glycosides by epoxidation of partially unblocked L-configured glycals. The stereochemical result depends on the orientation of the allylic hydroxyl group. A theoretical explanation is presented, based on the conformational preferences of the respective glycal half-chair conformations that were estimated by applying the BP density functional and a valence triple-zeta basis set.
Ernst
Christiane
C
Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität, Corrensstr. 40, D-48149, Münster, Germany.
Piacenza
Manuel
M
Grimme
Stefan
S
Klaffke
Werner
W
D002236:Carbohydrate Conformation; D004852:Epoxy Compounds / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D008958:Models, Molecular; D013237:Stereoisomerism
D004852:Epoxy Compounds; D006027:Glycosides