136282-42-3

Upstream product

• 119827-47-3 bis<6-(trifluoromethyl)benzotriazol-1-yl> methylphosphonate 
• 136740-88-0 (+/-)-2,3,6-tri-O-benzyl-myo-inositol 1,4-bis(dibenzyl phosphate) 
• 100-51-6 benzyl alcohol 
• 145794-00-9 Phosphorous acid dibenzyl ester (1R,2R,3S,4R,5R,6R)-2,3,6-tris-benzyloxy-4-(bis-benzyloxy-phosphanyloxy)-5-(4-methoxy-benzyloxy)-cyclohexyl ester 
• 138328-95-7 C₃₃H₄₂O₇ 
• 100-39-0 benzyl bromide 
• 138328-96-8 (+/-)-1,4-di-O-allyl-6-O-benzyl-5-O-p-methoxybenzyl-myo-inositol 
• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 117666-29-2 (+/-)-3,6-di-O-allyl-4-O-benzyl-1,2-O-cyclohexylidene-myo-inositol 
• 138329-00-7 (+/-)-2,3,6-tri-O-benzyl-5-O-p-methoxybenzyl-myo-inositol 1,4-bis(dibenzyl phosphate) 
• 145793-98-2 (+/-)-2,3,6-tri-O-benzyl-5-O-p-methoxybenzyl-1,4-di-O-trans-prop-1-enyl-myo-inositol 
• 138328-97-9 (+/-)-1,4-di-O-allyl-2,3,6-tri-O-benzyl-5-O-p-methoxybenzyl-myo-inositol 
• 138328-98-0 (+/-)-2,3,6-tri-O-benzyl-5-O-p-methoxybenzyl-myo-inositol 
• 112204-05-4 (+/-)-3,6-di-O-allyl-1,2-O-cyclohexylidene-myo-inositol 

Downstream Products

• 138382-82-8 myo-inositol 3-(methylphosphonate) 1,4-bis(phosphate) 

Relevant 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

(+/-)-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 5-phosphonate analogues of myo-inositol 1,4,5-trisphosphate: Possible intracellular calcium antagonists

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.

Synthesis of racemic 3-methylphosphonate analogues of myo-inositol 3,4-bis- and 1,3,4-trisphosphate

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.