“…Filigree experiments on targeted introduction of protective groups into the cyclitol system followed by phosphorylation, giving rise to myoinositols phosphites containing up to five phosphorus atoms, have been described in a number of studies. Phosphorus amide 31 , , dibenzyl N , N -dialkylphosphoramidites, − and o -xylylenyl N , N -dialkylphosphoramidites , were recommended as phosphorylating reagents for this purpose. The last-mentioned reagents are the most convenient.…”
“…Filigree experiments on targeted introduction of protective groups into the cyclitol system followed by phosphorylation, giving rise to myoinositols phosphites containing up to five phosphorus atoms, have been described in a number of studies. Phosphorus amide 31 , , dibenzyl N , N -dialkylphosphoramidites, − and o -xylylenyl N , N -dialkylphosphoramidites , were recommended as phosphorylating reagents for this purpose. The last-mentioned reagents are the most convenient.…”
“…To resolve the regioselectivity issue, we employed the Sn (IV) catalysts because Sn (IV) catalysts are known to form the complex with cis -diols in a regioselective manner and increase their reactivity . After systematic exploratory experiments (varying the equivalents of BDMDAP, temperature, solvents, and activators; SI, Table 2), we found that 1 equiv of BDMDAP in NMP as solvent at 80 °C afforded 75% conversion to cyclophosphate product 4 (SI, Table 2, entry 19).…”
Bis(dimethylamino)phosphorodiamidate
(BDMDAP) enables an efficient
and one-pot cyclophosphorylation of vicinal cis-diol
moiety of polyol-organics of biological importance without the need
for protecting group chemistry and is amenable to large-scale reactions.
The utility of this reagent is demonstrated through the synthesis
of high-value targets such as cyclic phosphates of myo-inositol, nucleosides, metabolites, and drug molecules.
A Simple Synthesis of D-myo-Inositol 4-Phosphate and D-myo-Inositol 6-Phosphate.--(IACOBUCCI, S.; D'ALARCAO, M.; Synth. Commun. 24 (1994) 6, 809-817; Michael Chem. Lab., Dep. Chem., Tufts Univ., Medford, MA 02155, USA; EN)
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