The preparation and phosphorylation of 2,5- and 1D-2,6-di-O-benzyl-myo-inositol.
1,3,4,6-Tetra-O-allyl-myo-inositol was converted into the 2,5-di-O-benzyl- and 2,5-di-O-p-methoxybenzyl ethers, and the products were deallylated to give the 2,5-di-O-benzyl (and p-methoxybenzyl) ethers of myo-inositol, which were converted into the mono-O-isopropylidene derivatives. Both the 2,5-di-O-benzyl ether and its mono-O-isopropylidene derivative were converted into the crystalline octa(2-cyanoethyl) ester of 2,5-di-O-benzyl-myo-inositol 1,3,4,6-tetrakisphosphate. (+-)-1,3,4,5-Tetra-O-allyl-myo-inositol was converted into (+-)-2,4-di-O-benzyl-myo-inositol which gave a separable mixture of the 1,6- and 5,6-O-isopropylidene derivatives. The 1,6-O-isopropylidene derivative was resolved via (-)- and (+)-omega-camphanates and was also converted into (+-)-2,6-di-O-benzyl-1,5-di-O-p-methoxybenzyl-myo-inositol, which was resolved via the (-)-omega-camphanates. The 5,6-O-isopropylidene derivative and 1,3-di-O-allyl-myo-inositol were converted into (+-)-1,3-di-O-allyl-2,6-di-O-benzyl-myo-inositol, which was resolved as the (-)-omega-camphanates. 1D-1,3,4,5-Tetra-O-allyl-myo-inositol and the above described, relevant diaste reoisomers were converted into 1D-2,6-di-O-benzyl-myo-inositol which gave the syrupy octabenzyl ester of 1D-2,6-di-O-benzyl-myo-inositol 1,3,4,5-tetrakisphosphate.
Desai
T
T
Laboratory of Lipid and General Chemistry, National Institute for Medical Research, Mill Hill, London, Great Britain.
Gigg
J
J
Gigg
R
R
Payne
S
S
D001593:Benzyl Compounds / Q000138:chemical synthesis*; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007295:Inositol Phosphates / Q000138:chemical synthesis*; D007536:Isomerism; D010766:Phosphorylation
D001593:Benzyl Compounds; D007295:Inositol Phosphates; C076316:2,6-di-O-benzylmyoinositol; C076315:2,5-di-O-benzylmyoinositol; D007294:Inositol