Cyclohexylammonium (1R,2R)-1,2-epoxy-3-hydroxypropylphosphonate was conveniently synthesized from dibenzyl (1S,2R)-2,3-O-cyclohexylidene-1,2,3-trihydroxypropylphosphonate by a reaction sequence including mesylation, hydrolysis of acetal, intramolecular Williamson reaction, and hydrogenation in the presence of cyclohexylamine. For dibenzyl (1S,2R)-2,3-O-cyclohexylidene-1,2,3-trihydroxypropylphosphonates the same approach was not successful, since prior the epoxide-ring closure tritylation of HO-C3 in dibenzyl (1R,2R)-2,3-dihydroxy-1-mesyloxypropylphosphonate was necessary and the hydrogenolysis of dibenzyl (1S,2R)-1,2-epoxy-3-trityloxypropylphosphonate yielded a complex reaction mixture.
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