✍ Scribed by Arlen L Jeffery; Jae-Hun Kim; David F Wiemer
No coin nor oath required. For personal study only.
AbstractÐNonracemic amino alcohols derived from common amino acids have been used to assemble acyclic nucleoside and nucleotide analogues with control of absolute stereochemistry. Both (R)-and (S)-2-amino-1-propanol, readily available from d-or l-alanine, were used to prepare the nucleoside analogues (R)-and (S)-9-[1-methyl-2-hydroxyethyl]adenine, and then the nucleotide analogues (R)-and (S)-9-[1methyl-2-phosphonomethoxyethyl]adenine. In a similar fashion, the CBz derivative of l-threonine was used to prepare ®rst (1R,2R)-9-[1hydroxymethyl-2-hydroxypropyl]adenine, and then the bis phosphonomethoxy derivative. The bis phosphonate derived from threonine represents a unique structural hybrid of PMEA and PMPA, both of which have well established antiviral activity.
📜 SIMILAR VOLUMES
enyloxy]prop-2-enyl}cytosine have been prepared in good yield from uridine and 5-methyluridine by periodate cleavage followed by a double Wittig reaction which introduces two vinyl groups. The thymine derivative underwent ring closure metathesis to give a novel synthesis of d4T.