The allyl group for protection in carbohydrate chemistry. Part 18. Allyl and benzyl ethers of myo-inositol. Intermediates for the synthesis of myo-inositol trisphosphates

Abstract

Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for ‘temporary’ protection. The benzyl ethers are required as intermediates for the synthesis of the ‘second messenger,’ inositol 1,4,5-trisphosphate and its metabolite, inositol 1,3,4-trisphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.