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
1998; Elsevier BV; Volume: 39; Issue: 46 Linguagem: Inglês
10.1016/s0040-4039(98)01909-1
ISSN1873-3581
Autores Tópico(s)Alkaline Phosphatase Research Studies
Resumo(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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