Darstellung von phosphorylierten Glucosiden durch Umsetzung am Glucosegerust sowie am Aglycon

摘要

The reaction of Me_2P (:X) H [X = O: 1; X = S: 4] with paraformaldehyde furnished the #alpha#-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-#alpha#-D-glucopyranoside 7. The spacer phosphorylated glucosyl derivatives 10 and 11 were formed in the reaction of #gamma#-bromopropyl-2, 3, 4, 6-tetra-O-benzyl-#beta#-D-glucopyranoside 9 with triethylphosphite and triphenylphosphine.