Multiply 13C-substituted monosaccharides: Synthesis of D-(1,5,6-13C3)glucose and D-(2,5,6-13C3)glucose

Article abstract of DOI:10.1016/0008-6215(92)84074-3

D-(1,5,6-¹³C₃)Glucose (7) has been synthesized by a six-step chemical method. D-(1,2-¹³C₂)Mannose (1) was converted to methyl D-(1,2-¹³C₂)mannopyranosides (2), and 2 was oxidized with Pt-C and O₂ to give methyl D-(1,2-¹³C₂)mannopyranuronides (3). After purification by anion-exchange chromatography, 3 was hydrolyzed to give D-(1,2-¹³C₂)mannuronic acid (4), and 4 was converted to D-(5,6-¹³C₂)mannonic acid (5) with NaBH₄. Ruff degradation of 5 gave D-(4,5-¹³C₂)arabinose (6), and 6 was converted to D-(1,5,6-¹³C₃) glucose (7) and D-(1,5,6-¹³C₃)mannose (8) by cyanohydrin reduction. D-(2,5,6-¹³C₃)Glucose (9) was prepared from 8 by molybdate-catalyzed epimerization.