The preparation of intermediates for the synthesis of 1d-myo-inositol 1,4,5- and 2,4,5-trisphosphates, 1,4-bisphosphate 5-phosphorothioate, and 4,5-bisphosphate 1-phosphorothioate from 1d-3,6-di-O-benzyl-1,2-O-isopropylidene-myo-inositol☆☆☆

Add time:08/18/2019    Source:sciencedirect.com

The preparation of 1d-1,6-di-O-benzyl-2,5-di-O-p-methoxybenzyl-myo-inositol is described. This compound and 1d-3,6-di-O-benzyl-1,2-O-isopropylidene-myo-inositol were converted into 1d-1,3,6-tri-O-benzyl-myo-inositol which was phosphorylated to give an intermediate for the synthesis of 1d-myo-inositol 2,4,5-trisphosphate. 1d-3,6-Di-O-benzyl-1,2-O-isopropylidene-myo-inositol was converted into 1d-2,3,6-tri-O-benzyl-myo-inositol (an intermediate for the synthesis of 1d-myo-inositol 1,4,5-trisphosphate) and 1d-2,3,6-tri-O-benzyl-1-O-p-methoxybenzyl-myo-inositol (an intermediate for the synthesis of the 1-phosphorothioate analogue of 1d-myo-inositol 1,4,5-trisphosphate). 1d-3,6-Di-O-benzyl-1,2-O-isopropylidene-myo-inositol was also converted into 1d-2,3,6-tri-O-benzyl-5-O-p-methoxybenzyl[and -5-O(cis-prop-1-enyl)]-myo-inositol both of which are intermediates for the synthesis of the 5-phosphorothioate analogue of 1d-myo-inositol 1,4,5-trisphosphate. The synthesis of 1d-2,3,6-tri-O-benzyl-myo-inositol 1,4-bis(dibenzyl phosphate) 5-(dibenzyl phosphorothioate) from 1d-2,3,6-tri-O-benzyl-myo-inositol 1,4-bis(dibenzyl phosphate) is described.

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