Development of water-atomised alloy steel powders : J.M. Cui et al. (Laiwu Iron and Steel PM Co. Ltd., Shandong Laiwu, China.) PM Industry, vol 11, no 4, 2001, 18–21. In Chinese

Abstract

Novel, structurally modified potential mimics of the second messenger d-myo-inositol 1,4,5-trisphosphate, based on the biologically active regioisomer d-myo-inositol 1,4,6-trisphosphate, were synthesised. dl-5-O-Benzyl-1,4,6-tri-O-p-methoxybenzyl-myo-inositol was the key intermediate for the preparation of the following compounds: dl-3-deoxy-, dl-3-deoxy-2-O-methyl-, dl-3-O-(2-hydroxyethyl)-, dl-3-O-(3-hydroxypropyl)- and dl-3-O-(4-hydroxybutyl)-myo-inositol 1,4,6-trisphosphate. dl-1,4,6-Tri-O -allyl-5-O-benzyl-myo-inositol was used to prepare dl-2-O-methyl-myo-inositol 1,4,6-trisphosphate. Deoxy-compounds were prepared by reduction of the corresponding tosylated intermediate using Super Hydride. The hydroxyalkyl groups were introduced at the C-3 of myo-inositol using the corresponding benzyl protected hydroxy alkyl bromide via the cis-2,3-O-dibutylstannylene acetal.Methylation and benzylation at C-2 was accomplished using methyl iodide and benzyl bromide, respectively, in the presence of sodium hydride. Deblocking of p-methoxybenzyl groups was accomplished with TFA in dichloromethane and the allyl groups were removed by isomerisation to the cis-prop-1-enyl derivative, which was hydrolysed under acidic conditions to give the corresponding 1,4,6-triol.The 1,4,6-triols were phosphitylated with the P(III) reagent bis(benzyloxy)(diisopropylamino)phosphine in the presence of 1H-tetrazole then oxidised with 3-chloroperoxybenzoic acid followed by deblocking by hydrogenolysis to give dl-2-O-methyl-, dl-3-O-deoxy-, dl-3-O-deoxy-2-O-methyl-, dl-3-O-(2-hydroxyethyl)-, dl-3-O-(3-hydroxypropyl)- and dl-3-O-(4-hydroxybutyl)-myo-inositol 1,4,6-trisphosphate, respectively.