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Scaleable and efficient synthesis of 2'-deoxy-2'-N-phthaloyl nucleoside phosphoramidites for oligonucleotide
Alexander Karpeisky1, David Sweedler, Peter Haeberli
1Department of Chemistry and Biochemistry, Ribozyme Pharmaceuticals Inc., Boulder, CO 80301, USA. alkarp@mindspring.com
Bioorganic & Medicinal Chemistry Letters
|October 24, 2002
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.