1207730-45-7Relevant articles and documents
Novel formal synthesis of stereospecifically C-6 deuterated d-glucose employing configurationally stable alkoxymethyllithiums
Kapeller, Dagmar C.,Hammerschmidt, Friedrich
experimental part, p. 591 - 598 (2010/09/05)
The synthesis and testing of configurational stability of chirally monodeuterated PMB- and THP-substituted oxymethyllithiums are described. Macroscopically they are configurationally stable up to -35 °C, the limit of their chemical stability, and microscopically even up to 0 °C. Furthermore, THP-protected oxy-[D1]methyllithium has been applied in the formal synthesis of (6R)-[6-D1]-d-glucose (four steps, 40% yield), an example of its use as a homochiral hydroxymethyl synthon.