Synthesis of 6-amino-3,5-deoxyinositol 1-phosphates via (1R,2R,4R,6S)-1,6-Epoxy-2,4-bis-Benzyloxycyclohexane (cas 16224-09-2) aminolysis in aqueous ytterbium triflate solution

Add time:07/29/2019    Source:sciencedirect.com

(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 uunder 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.

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