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-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.
Laboratory of Lipid and General Chemistry, National Institute for Medical Research, London, United Kingdom.
T
T
Desai
J
J
Gigg
R
R
Gigg
E
E
Martín-Zamora
D007294:Inositol / Q000031:analogs & derivatives* / Q000737:chemistry; D015544:Inositol 1,4,5-Trisphosphate / Q000138:chemical synthesis*; D007295:Inositol Phosphates / Q000138:chemical synthesis*; D015394:Molecular Structure; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis*
C090303:3,6-di-O-benzyl-1,2-O-isopropylideneinositol; D007295:Inositol Phosphates; D009946:Organothiophosphorus Compounds; C090314:inositol 4,5-bisphosphate 1-phosphorothioate; C066055:inositol 1,4-bisphosphate 5-phosphorothioate; D007294:Inositol; D015544:Inositol 1,4,5-Trisphosphate; C062616:inositol 2,4,5-trisphosphate