Scaleable and efficient synthesis of 2'-deoxy-2'-N-phthaloyl nucleoside phosphoramidites for oligonucleotide synthesis.
2'-Deoxy-2'-N-phthaloyl nucleosides were prepared from arabino nucleosides by triflate displacement with phthalimide in the presence of DBU. The corresponding phosphoramidites suitable for automated oligonucleotide synthesis were also synthesized. The scalability of described procedures was demonstrated on a 100-g scale preparation of 2'-deoxy-2'-amino-C phosphoramidite.
Karpeisky
Alexander
A
Department of Chemistry and Biochemistry, Ribozyme Pharmaceuticals Inc., Boulder, CO 80301, USA. alkarp@mindspring.com
Sweedler
David
D
Haeberli
Peter
P
Read
Javier
J
Jarvis
Keith
K
Beigelman
Leonid
L
D001087:Arabinonucleosides / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods; D008698:Mesylates; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D011692:Puromycin Aminonucleoside / Q000138:chemical synthesis
D001087:Arabinonucleosides; D008698:Mesylates; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D011692:Puromycin Aminonucleoside; C012077:trifluoromethanesulfonic acid