title: Scaleable and efficient synthesis of 2'-deoxy-2'-N-phthaloyl nucleoside phosphoramidites for oligonucleotide synthesis.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Ribozyme Pharmaceuticals Inc., Boulder, CO 80301, USA. alkarp@mindspring.com
authors.forename: Alexander
authors.initials: A
authors.lastname: Karpeisky
authors.forename: David
authors.initials: D
authors.lastname: Sweedler
authors.forename: Peter
authors.initials: P
authors.lastname: Haeberli
authors.forename: Javier
authors.initials: J
authors.lastname: Read
authors.forename: Keith
authors.initials: K
authors.lastname: Jarvis
authors.forename: Leonid
authors.initials: L
authors.lastname: Beigelman
mesh_terms: 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
chemical_list: D001087:Arabinonucleosides; D008698:Mesylates; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D011692:Puromycin Aminonucleoside; C012077:trifluoromethanesulfonic acid