112204-06-5Relevant academic research and scientific papers
Synthesis of racemic 5-phosphonate analogues of myo-inositol 1,4,5-tris- and 1,3,4,5-tetrakis-phosphate
Dreef, Cornelis E.,Jansze, Jan-Pieter,Elie, Cornelius J. J.,Marel, Gijs A. van der,Boom, Jacques H. van
, p. 37 - 50 (2007/10/02)
(+/-)-2,3,6-Tri-O-benzyl-5-O-p-methoxybenzyl-myo-inositol and (+/-)-2,6-di-O-benzyl-5-O-p-methoxybenzyl-myo-inositol, accessible readily from (+/-)-3,6-di-O-allyl-1,2-O-cyclohexylidene-myo-inositol, were phosphitylated with dibenzyl N,N-di-isopropylphosph
Synthesis of racemic 3-methylphosphonate analogues of myo-inositol 3,4-bis- and 1,3,4-trisphosphate
Dreef,Tuinman,Lefeber,Elie,Van Der Marel,Van Boom
, p. 4709 - 4722 (2007/10/02)
The partially benzyl protected myo-inositol derivatives 11a and 11b, the C-4 and C-1,4 hydroxyl function(s) of which are protected with temporary trans-prop-1-enyl protecting group(s), were readily converted into the respective title compounds 18a and 18b by sequential methylphosphonylation, mild cleavage of the trans-prop-1-enyl group(s), phosphorylation and removal of all permanent benzyl protecting groups.
Synthesis of 5-phosphonate analogues of myo-inositol 1,4,5-trisphosphate: Possible intracellular calcium antagonists
Dreef,Schiebler,Van der Marel,Van Boom
, p. 6021 - 6024 (2007/10/02)
The racemic 5-phosphonate analogues IV and V of myo-inositol 1,4,5-trisphosphate were readily accessible by bisphosphorylation of the common precursor 6, removal of the p-methoxybenzyl group, phosphonylation and subsequent hydrogenolysis of the benzyl protecting groups. The methylphosphonate analogue IV acted as a calcium antagonist in permeabilized human platelets, whereas the (difluoromethyl)phosphonate V exhibited only very little antagonistic activity.
TOTAL SYNTHESIS OF OPTICALLY ACTIVE MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND MYO-INOSITOL 1,3,4,5-TETRAKISPHOSPHATE
Dreef, C. E.,Tuinman, R. J.,Elie, C. J. J.,Marel, G. A. van der,Boom, J. H. van
, p. 395 - 397 (2007/10/02)
A convenient approach to the preparation of the title compounds illustrating selective protection, optical resolution and phosphorylation is presented.
SYNTHESIS OF RACEMIC MYO-INOSITOL 1,3,4-TRIPHOSPHATE VIA A PHOSPHITE-TRIESTER APPROACH
Dreef, C. E.,Marel, G. A. van der,Boom, J. H. van
, p. 161 - 162 (2007/10/02)
Phosphitylation of (+/-)- 2,4,5-tri-O-benzyl-myo-Inositol with bis(2-cyanoethyl)chlorophosphine gave, after oxidation followed by basic hydrolysis and subsequently hydrogenolysis, (+/-)-myo-Inositol 1,3,4-triphosphate.
