Asymmetric synthesis of both enantiomers of two acyclic nucleoside analogues related to d4T and acyclovir

The enantiomers of 1-{[(2-hydroxy-1-phenyl)ethoxy]methyl}thymine and 9-{[(2-hydroxy-1-phenyl)ethoxy]methyl}guanine have been obtained in high yield in five steps from ( R)- and ( S)-1-phenylethan-1,2-diol. These chiral compounds are acyclic nucleoside analogues of d4T and acyclovir, respectively. Gr...

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Bibliographic Details
Published in:Tetrahedron letters 2002-02, Vol.43 (6), p.989-991
Main Authors: Ewing, David F, Glaçon, Virginie, Mackenzie, Grahame, Len, Christophe
Format: Article
Language:English
Subjects:
acyclic nucleosides
acyclovir
asymmetric dihydroxylation
d4T
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Summary:The enantiomers of 1-{[(2-hydroxy-1-phenyl)ethoxy]methyl}thymine and 9-{[(2-hydroxy-1-phenyl)ethoxy]methyl}guanine have been obtained in high yield in five steps from ( R)- and ( S)-1-phenylethan-1,2-diol. These chiral compounds are acyclic nucleoside analogues of d4T and acyclovir, respectively. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)02298-5