Synthesis of 6-amino-3,5-deoxyinositol 1-phosphates via (1R,2R,4R,6S)- 1,6-epoxy-2,4-bis-benzyloxycyclohexane aminolysis in aqueous ytterbium triflate solution

Article abstract of DOI:10.1016/S0040-4039(98)01909-1

(1R,2R,4R,6S)-1,6-Epoxy-2,4-bis-benzyloxycyclohexane was prepared from (-)-quinic acid and this, and cyclohexene oxide, were treated with various N- nucleophiles under a variety of conditions. In aqueous solution containing catalytic amounts of ytterbium (III) triflate, ammonia and alkylamines reacted smoothly to give the required trans-1,2-amino alcohols in quantitative recovery. Conversion of the 6-amino-2,4-bis-benzyloxycyclohexan- 1-ols to 6-amino-1,2,4-trihydroxycyclohexane 1-phosphates, probes for the mechanism of inositol monophosphatase, was achieved in good overall yield.