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- W2078093823 abstract "1,6-Anhydro-3,4-O-isopropyliden-β-D-lyxo-hexopyranos-2-ulose (1) reagiert unter Abramov-Bedingungen mit Dialkylphosphiten stark bevorzugt zu den 2-Phosphonaten 2 und 3 der talo-Konfiguration. 1,6-Anhydro-2,3-O-isopropyliden-β-D-lyxo-hexopyranos-4-ulose (17) liefert bei gleicher Reaktion stark bevorzugt die 4-Phosphonate 18 und 19 ebenfalls der talo-Konfiguration. Das durch Umlagerung aus dem 3,4-Acetal 2 gewinnbare 2,3-Acetal 8 läßt sich erneut zur 4-Ulose 20 oxidieren. Abramov-Reaktion von 20 ergibt ein trennbares Gemisch von 2,4-Bis-phosphonat-Zuckern 21 und 22 der manno- und talo-Konfiguration im Verhältnis 1:4. Die Abhängigkeit der PCOH-Kopplung vom Diederwinkel wird diskutiert und hierfür eine Beziehung vorgeschlagen. Phosphorus-containing Carbohydrates, VII. Synthesis of α-Hydroxyphosphonates of 1,6-Anhydrohexoses. Investigations of PCOH Coupling. 1,6-Anhydro-3,4-O-isopropylidene-β-D-lyxo-hexopyranos-2-ulose (1) reacts with dialkyl phosphites under Abramov-conditions to give predominantly the 2-phosphonato derivatives 2 and 3 having the talo configuration. 1,6-Anhydro-2,3-O-isopropylidene-β-D-lyxo-hexopyranos-4-ulose (17) affords under the same conditions predominantly the 4-phosphonates 18 and 19 also having talo configuration. The 2,3-acetal 8 obtained by rearrangement of the 3,4-acetal 2 may be oxidized to the 4-ulose 20. Abramov-reaction of 20 yields a mixture of two 2,4-diphosphonates which was separated to give 21 and 22 in the ratio 1:4 having the manno and talo configuration, respectively. The dependence of PCOH coupling on dihedral angle is discussed and a relationship proposed." @default.
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- W2078093823 date "1973-07-01" @default.
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- W2078093823 title "Phosphorhaltige Kohlenhydrate, VII. Synthese von α‐Hydroxyphosphonaten der 1,6‐Anhydrohexosen. Untersuchungen über die PCOH‐Kopplung" @default.
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- W2078093823 doi "https://doi.org/10.1002/cber.19731060706" @default.
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