SYNTHESIS OF 6-AMINO-3-5-DEOXYINOSITOL 1-PHOSPHATES VIA R,2R,4R,6S)-1,6-EPOXY-2,4-BIS-BENZYLOXYCYCLOHEXANE AMINOLYSIS IN AQUEOUS YTTERBIUM TRIFLATE SOLUTION

R,2R,4R,6S)-1,6-Epoxy-2,4-bis-benzyloxycyclohexane was prepared from ( -)-quinic acid and this, and cyclohexene oxide, were treated with vari ous 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 alco hols in quantitative recovery. Conversion of the 6-amino-2,4-bis-benzy loxycyclohexan-1-ols to 6-amino-1,2,4-trihydroxycyclohexane 1-phosphat es, probes for the mechanism of inositol monophosphatase, was achieved in good overall yield. (C) 1998 Elsevier Science Ltd. All rights rese rved.