848421-28-3Relevant academic research and scientific papers
Synthesis of C-glycosides related to glycero-β-d-manno-heptoses
Graziani, Andrea,Amer, Hassan,Zamyatina, Alla,Hofinger, Andreas,Kosma, Paul
, p. 167 - 175 (2005)
Reducing heptopyranoses of the d-glycero-d-manno- and l-glycero-d-manno- configuration were converted in good overall yields into β-anomeric C-glycosides via condensation with pentane-2,4-dione, followed by sodium methoxide-induced enrichment of the β-anomeric products and subsequent O-acetylation. The resulting 2-oxo-propyl glycosides were further transformed into separable ～1:1 diastereomeric mixtures of (S)-and (R)-2-hydroxy derivatives. The configuration of the additional stereogenic centre was assigned on the basis of NMR data obtained from the corresponding Dale-Mosher esters. Finally, phosphorylation of the d-glycero-d-manno-heptose analogues using the phosphoramidite procedure and deprotection furnished the (S)- and (R)-2-phosphate derivatives in good yields. The compounds serve as substrate analogues for enzymes involved in bacterial ADP heptose biosynthesis and glycosyl transfer reactions.
