PMID- 3697146
OWN - NLM
STAT- MEDLINE
DCOM- 19880127
LR  - 20201209
IS  - 0261-3166 (Print)
IS  - 0261-3166 (Linking)
IP  - 18
DP  - 1987
TI  - Stereospecific syntheses of 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)adenine 
      (HPMPA).
PG  - 33-6
AB  - 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.
FAU - Holy, A
AU  - Holy A
AD  - Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of 
      Sciences, Praha.
FAU - Rosenberg, I
AU  - Rosenberg I
LA  - eng
PT  - Journal Article
PL  - England
TA  - Nucleic Acids Symp Ser
JT  - Nucleic acids symposium series
JID - 8007206
RN  - 0 (Antiviral Agents)
RN  - 0 (Indicators and Reagents)
RN  - 0 (Organophosphonates)
RN  - 0 (Organophosphorus Compounds)
RN  - CJC8PO1KQ3 (9-(S)-(3-hydroxy-2-(phosphonomethoxy)propyl)adenine)
RN  - JAC85A2161 (Adenine)
SB  - IM
MH  - Adenine/*analogs & derivatives/chemical synthesis
MH  - Antiviral Agents/*chemical synthesis
MH  - Indicators and Reagents
MH  - *Organophosphonates
MH  - *Organophosphorus Compounds
MH  - Stereoisomerism
EDAT- 1987/01/01 00:00
MHDA- 1987/01/01 00:01
CRDT- 1987/01/01 00:00
PHST- 1987/01/01 00:00 [pubmed]
PHST- 1987/01/01 00:01 [medline]
PHST- 1987/01/01 00:00 [entrez]
PST - ppublish
SO  - Nucleic Acids Symp Ser. 1987;(18):33-6.