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• W2072558427 abstract "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." @default.
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• W2072558427 date "2005-01-01" @default.
• W2072558427 modified "2023-09-30" @default.
• W2072558427 title "Synthesis of C-glycosides related to glycero-β-d-manno-heptoses" @default.
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• W2072558427 doi "https://doi.org/10.1016/j.tetasy.2004.11.065" @default.
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