Synthesis and biological activities of (4,6-di-O-phosphonato-β-D-mannopyranosyl)methylphosphonate as an analogue of 1L-myo-inositol 1,4,5-trisphosphate

Article abstract of DOI:10.1016/0008-6215(94)80020-0

The synthesis of the α and β anomers of the title compound (1) was accomplished from D-mannose.In the key step, the phosphonate analogues of the mannopyranosyl phosphates were prepared by a direct Wadsworth-Emmons condensation of a protected mannose derivative (8) with tetraethyl methylenebisphosphonate under two-phase conditions.In vitro bioassays have shown that the β-anomer (1a) is a potent inhibitor of Ins(1,4,5)P3 3- kinase and inhibits other enzymes.