Stereoselective synthesis of inositol mono, bis and trisphosphate analogues from 6-deoxy-D-inositol precursors.

The synthesis of opticaly pure deoxy-myo-inositol mono, bis and trisphospha te analogues is described from 4-O-benzyl-2,3-di-O-cyclohexylidene-6-deoxy- myo-inositol and corresponding 1,5 epimer chiro-inositol. These precursors, which derive from galactose, are used to accede to a variety of cyclitol i ntermediates employing protection/deprotection sequence. The phosphorylatio n procedure was performed to produce free and original substituted phosphat e derivatives aimed to be incorporated through the lipidic cell membrane fo r in vivo evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.