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Synthesis of Phosphorylated Glucosides through Reaction at the Glucose Framework and at the Aglycon

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Darstellung von phosphorylierten Glucosiden durch Umsetzung am Glucoseger ¨ust sowie am Aglycon

Synthesis of Phosphorylated Glucosides through Reaction at the Glucose Framework and at the Aglycon

Carsten Melnicky, Ion Neda und Reinhard Schmutzler

Institut f¨ur Anorganische und Analytische Chemie der Technischen Universit¨at, Postfach 3329, D-38023 Braunschweig, Germany

Sonderdruckanforderungen an R. Schmutzler.

Fax: +49 531 391 5387. E-mail: r.schmutzler@tu-bs.de

Z. Naturforsch.54 b,1547–1552 (1999); eingegangen am 13. Oktober 1999 Glucopyranoside, Phosphorylation

The reaction of Me2P(:X)H [X = O:1; X = S:4] with paraformaldehyde furnished the- hydroxyphosphine oxide2and sulfide5which, upon treatment with p-toluenesulfonyl chloride, were converted into the tosylated derivatives3and6. The diphosphorylated glucosyl compound 8was synthesized by reaction of two equivalents of tosylated phosphine oxide3with benzyl 4,6- O-benzyliden--D-glucopyranoside7. The spacer phosphorylated glucosyl derivatives10and 11were formed in the reaction of-bromopropyl-2,3,4,6-tetra-O-benzyl--D-glucopyranoside 9with triethylphosphite and triphenylphosphine.

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