532392-39-5Relevant articles and documents
Epoxidation of C-branched glycals: Unexpected stereochemical results and their theoretical rationale
Ernst, Christiane,Piacenza, Manuel,Grimme, Stefan,Klaffke, Werner
, p. 231 - 236 (2003)
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-ζ basis set.