635312-24-2Relevant academic research and scientific papers
Diastereoselective synthesis of (aryloxy)phosphoramidate prodrugs
Arbelo Roman, Cristina,Wasserthal, Philip,Balzarini, Jan,Meier, Chris
experimental part, p. 4899 - 4909 (2011/10/31)
The first diastereoselective synthesis of aryloxyphosphoramidate prodrugs of 3′-deoxy-2′,3′-didehydrothymidinemonophosphate (d4TMP) was recently reported. The synthetic approach utilized the chiral auxiliary (S)-4-isopropylthiazolidine-2-thione (2). For this strategy, a stereochemically pure phosphorodiamidate intermediate was needed. The diastereoselective formation of this key compound was investigated by using different phenols and L-alanine methyl or benzyl ester. Generally, the reaction with 3- or 4-substituted phenols led to significantly better diastereoselectivities compared to their 2-substituted counterparts. Moreover, variation of the ester group in the amino acid residue resulted in no significant differences with regard to the obtained diastereoselectivity. From the reported results, a model for the transition state was elaborated. Finally, eight new (S P)-arylphosphoramidates were synthesized with very high diastereoselectivities (up to ≥ 95 % de) and tested for their anti-HIV potency, showing a tendency for higher antiviral activity from the (S P) diastereomers.
Synthesis, separation and anti-HIV activity of distereoisomers of N-[p-(4-bromophenyl)-2',3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanine methyl ester (stampidine)
Venkatachalam, Taracad K.,Qazi, Sanjive,Uckun, Fatih M.
, p. 152 - 158 (2007/10/03)
The distereoisomers of stampidine (STAMP, DDE-113, HI-113, N-[p-(4-bromophenyi)-2',3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanine methyl ester, CAS 217178-62-6) were separated using two different procedures. The first method involved separation of the iso
