Darstellung von phosphorylierten Glucosiden durch Umsetzung am Glucosegerüst sowie am Aglycon / Synthesis of Phosphorylated Glucosides through Reaction at the Glucose Framework and at the Aglycon

Abstract

The reaction of Me2P(:X)H [X = O: 1; X = S: 4] with paraformaldehyde furnished the α - hydroxyphosphine oxide 2 and sulfide 5 which, upon treatment with p-toluenesulfonyl chloride, were converted into the tosylated derivatives 3 and 6. The diphosphorylated glucosyl compound 8 was synthesized by reaction of two equivalents of tosylated phosphine oxide 3 with benzyl 4,6- O-benzyliden-α-D-glucopyranoside 7. The spacer phosphorylated glucosyl derivatives 10 and 11 were formed in the reaction of γ -bromopropyl-2,3,4,6-tetra-0 -benzyl-β-D-glucopyranoside 9 with triethylphosphite and triphenylphosphine.