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
M. Beaton et D. Gani, 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, Tetrahedron letters, 39(46), 1998, pp. 8549-8552
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.