Carboranyl Oligonucleotides. 1. Synthesis of Thymidine(3',5')thymidine (o-Carboran-1-ylmethyl)phosphonate

Article abstract of DOI:10.1021/jo00076a001

Using methyl (o-carboran-1-ylmethyl)phosphonate 6 as a novel and versatile borophosphonylating agent, 5'-O-(monomethoxytrityl)thymidine 3'-O- (8) and thymidine(3',5')thymidine (o-carboran-1-ylmethyl)phosphonate (12) were synthesized.The internucleotide (o-carboran-1-ylmethyl)phosphonate linkage was resistant to cleavage by phosphorodiesterases.The dinucleotide 12 represents a new class of modified lipophilic oligonucleotide-bearing carboranyl residue, designed as a carrier for boron neutron capture therapy and for potential use in antisense oligonucleotide technology.