115514-28-8Relevant articles and documents
Synthesis of C-Glucosides by Reactions of Glucosyl Halides with Organocuprates.
Bihovsky Ron,Selick Caryn,Giusti Irena
, p. 4026 - 4031 (2007/10/02)
Lithium dimethylcuprate reacts with trans-2-chloro-6-methyltetrahydropyran (1) via nucleophilic substitution predominantly with inversion of configuration to afford cis-2,6-dimethyltetrahydropyran (2).Similarly, lithium dialkylcuprates displace protected α-glucosyl bromides (5) with inversion to afford the β-C-glucosides, β-1-alkyl-1,5-anhydroglucitols (6).In contrast, Grignard reagents gave mixtures of α- and β- glucosides 6 and 7, while organolithium reagents gave only elimination to 9.