Novel formal synthesis of stereospecifically C-6 deuterated d-glucose employing configurationally stable alkoxymethyllithiums
作者:Dagmar C. Kapeller、Friedrich Hammerschmidt
DOI:10.1016/j.tet.2009.11.084
日期:2010.1
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
描述了手性单氘代PMB和THP取代的氧甲基锂的合成和构型稳定性的测试。在宏观上,它们在高达-35°C(化学稳定性的极限)下具有构型稳定性,在微观上甚至高达0°C。此外,THP-保护的氧基- [ d 1 ]甲基锂(6正式合成已施加ř) - [6- d 1 ] - d -葡萄糖(四个步骤,40%产率),作为其使用的一个例子纯手性羟甲基合成子。