Arlen L Jeffery, Jae‐Hun Kim, D. Wiemer
Jul 14, 2000
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron
Abstract
Abstract Nonracemic 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-[1-methyl-2-phosphonomethoxyethyl]adenine. In a similar fashion, the CBz derivative of l -threonine was used to prepare first (1 R ,2 R )-9-[1-hydroxymethyl-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.