Stereospecific syntheses of 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA).
9-(S)-(3-Hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA) was prepared from 9-(S)-(2,3-dihydroxypropyl)adenine (DHPA) via its 3-O-chloromethanephosphonate. The latter compound is obtained by treatment of DHPA with chloromethanephosphonyl dichloride and the 3'-isomer separated from its 2'-congener by ion-exchange chromatography. The 3'-isomer is prepared selectively by the same method starting from 2',6-dibenzoyl derivative of DHPA. The 3'-ester is transformed to HPMPA by treatment with aqueous alkali. Alternatively, 9-(S)-(2-hydroxy-3-triphenylmethoxypropyl)-N6-benzoyladenine can be converted to HPMPA by reaction with dialkyl p-tolylsulfonyloxymethane-phosphonates in the presence of NaH followed by successive acid and alkaline treatment.
Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, Praha.
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Holý
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Rosenberg
D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D013237:Stereoisomerism
D000998:Antiviral Agents; D007202:Indicators and Reagents; D063065:Organophosphonates; D009943:Organophosphorus Compounds; C050127:9-(S)-(3-hydroxy-2-(phosphonomethoxy)propyl)adenine; D000225:Adenine