115072-68-9Relevant academic research and scientific papers
Synthesis of potent Ins(1,4,5)P3 5-phosphatase inhibitors by modification of myo-inositol 1,3,4,6-tetrakisphosphate
Mills, Stephen J.,Potter, Barry V. L.
, p. 4245 - 4253 (2007/10/03)
Three myo-inositol tetrakisphosphate analogues were synthesised based upon myo-inositol 1,3,4,6-tetrakisphosphate: 2,5-di-O-methyl myo-inositol-1,3,4,6-tetrakisphosphate 19 and its phosphorothioate derivative 22, together with myo-inositol 1,3,4,6 tetraki
Unambiguous Total Synthesis of the Enantiomers of myo-Inositol 1,3,4-Trisphosphate: 1L-myo-Inositol 1,3,4-Trisphosphate Mobilizes Intracellular Ca2+ in Limulus Photoreceptors
Riley, Andrew M.,Payne, Richard,Potter, Barry V. L.
, p. 3918 - 3927 (2007/10/02)
Syntheses of the enantiomers of myo-inositol 1,3,4-trisphosphate are described. 1,4-Di-O-allyl-myo-inositol was regioselectively p-methoxybenzylated at the 3-position to give 1,4-di-O-allyl-3-O-(p-methoxybenzyl)-myo-inositol followed by benzylation of the remaining free hydroxyl groups to give the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol.Removal of the p-methoxybenzyl and allyl groups gave 2,4,5-tri-O-benzyl-myo-inositol which was-phosphitylated with bis(benzyloxy)(diisopropylamino)phosphine to give the fully protected trisphosphite triester.Oxidation using tert-butyl hydroperoxide gave 2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol, and deprotection using sodium in liquid ammonia gave racemic myo-inositol 1,3,4-trisphosphate.Deprotection of the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol by isomerization of allyl groups followed by mild acid hydrolysis gave 2,4,5-tri-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol, which was converted to the diastereoisomeric bis-(-)-camphanates.The diastereoisomers were separated by column chromatography and the camphanates and the p-methoxybenzyl group removed by saponification and acid hydrolysis, respectively, for each diastereoisomer to give the enantiomers of 2,4,5-tri-O-benzyl-myo-inositol.The absolute configurations of the latter were established by conversion of 1L-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol to the known 1L-1,2,4,5,6-penta-O-benzyl-myo-inositol.Phosphorylation and deblocking gave the D- and L-enantiomers of myo-inositol 1,3,4-trisphosphate.Biological evaluation in Limulus photoreceptors showed that 1L-myo-inositol 1,3,4-trisphosphate was much more active than the D-enantiomer, producing repetitive bursts of depolarization due to mobilization of intra cellular calcium.
The allylation of dibutylstannylene derivatives of myo-inositol
Desai, Trupti,Gigg, Jill,Gigg, Roy,Payne, Sheila,Penades, Soledad,Rogers, Henry J.
, p. 197 - 209 (2007/10/02)
Reaction of myo-inositol or a mixture of racemic 1,4-, 1,6-, and 4,5-di-O-allyl-myo-inositol in acetonitrile with dibutyltin oxide and allyl bromide in the presence of tetrabutylammonium bromide gave, as the major products, a readily separable mixture of
THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE CHEMISTRY. PART 21. (+/-)-1,2:5,6- AND (+/-)-1,2:3,4-DI-O-ISOPROPYLIDENE-MYO-INOSITOL. THE UNUSUAL BEHAVIOUR OF CRYSTALS OF (+/-)-3,4-DI-O-ACETYL-1,2,5,6-TETRA-O-BENZYL-MYO-INOSITO ON HEATING AND COOLING: A '
Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
, p. 2411 - 2414 (2007/10/02)
Racemic 1,2-O-isopropylidene-myo-inositol was converted into a mixture of 1,2:5,6-, 1,2:3,4-, and 1,2:4,5-di-O-isopropylidene-myo-inositols which were resolved by g.l.c.The 1,2:4,5 and 1,2:5,6- isomers were isolated from the mixture as benzoate derivative
