A short, efficient synthesis of 2'-deoxypseudoisocytidine based on Heck-chemistry.
A novel synthesis of 2'-deoxypseudoisocytidine as well as of its phosphoramidite building block for oligonucleotide synthesis is presented. The synthesis is based on Heck-coupling between N-protected pseudoisocytosine and a silyl protected furanoid glycal. With this procedure the corresponding phosphoramidite building block is obtained in 5 steps and an overall yield of 28%.
Mayer
Alain
A
Department of Chemistry & Biochemistry, University of Bern, Bern, Switzerland.
Leumann
Christian J
CJ
D003841:Deoxycytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
C487122:N-benzoyl-2'-deoxypseudoisocytidine; D003841:Deoxycytidine