- The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates
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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-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 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.
- Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
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p. 423 - 430
(2007/10/02)
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- The Allyl Group for Protection in Carbohydrate Chemistry. Part 20. Synthesis of 1L-1-O-Methyl-myo-inositol by Resolution of (+/-)-1,2,4-Tri-O-benzyl-myo-inositol
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Racemic 1,2,4-tri-O-benzyl-myo-inositol was prepared by two new routes from (+/-)-1,4-di-O-benzyl-5,6-O-isopropylidine-myo-inositol, one route involving the crystalline intermediate (+/-)-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidine-myo-inositol.Oxidati
- Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
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p. 1757 - 1762
(2007/10/02)
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- Cyclitol Reactions, V. - Synthesis of Enantiomerically Pure Valienamine from Quebrachitol
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An enantioselective synthesis of Valienamine (86) from quebrachitol (L-2O-methyl-chiro-inositol) (1) is described.Valienamine (86) is an unsaturated branched-chain aminocyclitol found in the central structural unit of the antidiabetic drug acarbose.Techniques for the introduction of side chains, azido groups, and double bonds into inositol systems are investigated.The methods developed in this connection are applied in the synthesis of valienamine.
- Paulsen, Hans,Heiker, Fred R.
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p. 2180 - 2203
(2007/10/02)
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