Tetrahedron

Novel formal synthesis of stereospecifically C-6 deuterated d-glucose employing configurationally stable alkoxymethyllithiums

DC Kapeller, F Hammerschmidt

Index: Kapeller, Dagmar C.; Hammerschmidt, Friedrich Tetrahedron, 2010 , vol. 66, # 3 p. 591 - 598

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Citation Number: 5

Abstract

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 ...