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- W2068857526 abstract "Zucker-1-eno-phosphonate 1 und 4 lassen sich mit Natriumäthylat oder Piperidin umlagern in die Zucker-2-eno-phosphonate 2 + 3 und 5 + 6. Diese werden als cis-trans-Gemisch erhalten, in dem die trans-Form überwiegt. Als Enole gehen sie bei der Hydrolyse in Ketosen über. Die mit Dihydroxyaceton-phosphat und Ribulose-1-phosphat isosteren Phosphonate 9 und 12 mit stabiler C–P-Bindung sind auf diesem Wege zugänglich. Hydrierung der Zucker-1-eno-phosphonate ergibt die gesättigten Verbindungen 15 und 23. Durch Umesterung von Diäthylphosphonaten in Bis(trimethylsilyl)phosphonate und anschließende Hydrolyse mit Wasser sind die freien Zuckerphosphonsäuren zu erhalten. Phosphorus-containing Carbohydrates, XIII. Rearrangemnt of Sugar-1-enophosphonates to Sugar-2-enophosphonates Sugar-1-enophosphonates 1 and 4 can be rearranged by means of sodium ethoxide or piperidine to sugar-2-enophosphonates 2 + 3 and 5 + 6. These are obtained as a cis-trans-mixture with the trans-form predominating. As enols they yield ketoses under hydrolysis. The phosphonates 9 and 12 having a stable C–P-linkage which are isosteric with dihydroxyacetone phosphate and ribulose-1-phosphate are thus accessible. Hydrogenation of sugar-1-enophosphonates leads to saturated compounds 15 and 23. Transesterification of diethyl phosphonates to bis(trimethylsilyl) phosphonates and subsequent hydrolysis with water yields free sugar phosphonic acids." @default.
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- W2068857526 date "1975-05-01" @default.
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- W2068857526 title "Phosphorhaltige Kohlenhydrate, XIII. Umlagerung von Zucker‐1‐eno‐phosphonaten zu Zucker‐2‐eno‐phosphonaten" @default.
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- W2068857526 doi "https://doi.org/10.1002/cber.19751080541" @default.
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