Journal
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Volume 20, Issue 4-7, Pages 621-628Publisher
MARCEL DEKKER INC
DOI: 10.1081/NCN-100002338
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The practical synthesis of a mixed phenoxy-amidate derivative of PMPA with high oral bioavailability and favorable pharmacokinetics is described. The nonstereoselective synthetic route produces a 1:1 mixture of two diastereomers at phosphorous. Simulated moving bed chromatography using Chiralpak AS enabled kilo-scale isolation of the more potent diastereomer (GS-7340). The GS-7340 phosphorous chiral center was found to be (S) by X-ray crystallography.
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