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

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-inosito...

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Bibliographic Details
Published in:Carbohydrate research 1994-09, Vol.262 (1), p.59-77
Main Authors: Desai, T, Gigg, J, Gigg, R, Martín-Zamora, E
Format: Article
Language:English
Subjects:
Inositol - analogs & derivatives
Inositol - chemistry
Inositol 1,4,5-Trisphosphate - chemical synthesis
Inositol Phosphates - chemical synthesis
Molecular Structure
Organothiophosphorus Compounds - chemical synthesis
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Summary: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.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(94)84005-9