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Synthesis of (1 R ,2 R )‐ and (1 S ,2 R )‐1,2‐Epoxy‐3‐hydroxypropylphosphonates as Analogues of Fosfomycin
Author(s) -
Wróblewski Andrzej E.,
Szewczyk Eligia M.,
BaôkSypień Irena I.
Publication year - 2009
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200900044
Subject(s) - epoxide , chemistry , epoxy , acetal , cyclohexylamine , hydrogenolysis , intramolecular force , ring (chemistry) , medicinal chemistry , hydrolysis , stereochemistry , catalysis , organic chemistry
Cyclohexylammonium (1 R ,2 R )‐1,2‐epoxy‐3‐hydroxypropylphosphonate was conveniently synthesized from dibenzyl (1 S ,2 R )‐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 (1 S ,2 R )‐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 (1 R ,2 R )‐2,3‐dihydroxy‐1‐mesyloxypropylphosphonate was necessary and the hydrogenolysis of dibenzyl (1 S ,2 R )‐1,2‐epoxy‐3‐trityloxypropylphosphonate yielded a complex reaction mixture.