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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



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



Journal of the Chemical Society Perkin Transactions I (2): 423-430



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.

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Accession: 006598801

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DOI: 10.1039/p19870000423


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