An efficient synthesis of a new series of acyclonucleosides starting from beta-amino alcohols.
A series of new acyclonucleosides analogues 3 has been synthesized very efficiently in three steps starting from beta-amino alcohols 1. The key step of this process is a nucleophilic substitution with various nucleophiles on 2,2'-anhydronucleosides 2. The chemo- and stereoselectivities of this reaction are discussed. AM1 calculations sustained the observed chemoselectivity.
Agami
C
C
Laboratoire de Synthèse Asymétrique (UMR CNRS 7611), Université P. et M. Curie, Paris, France.
Dechoux
L
L
Hamon
L
L
Melaimi
M
M
D000605:Amino Alcohols / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000138:chemical synthesis; D011744:Pyrimidinones / Q000138:chemical synthesis; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000605:Amino Alcohols; D000998:Antiviral Agents; D011743:Pyrimidines; D011744:Pyrimidinones; D014498:Uracil