Synthesis of terphenylboronic acid derivatives and recognition of anomers of 2-deoxyribofuranoside

Article abstract of DOI:10.1246/cl.1996.537

A terphenylboronic acid 1 and its silylated derivative 2 are prepared from (2-nitrophenyl)acetic acid for the purpose of controlling stereochemistry of synthetic organic reactions. These boronic acids are found to recognize α and β-anomers of 2-deoxyribofuranosides. That is, when these boron compounds are added to a 1 : 1 mixture of α and β-t-butyl 5-O-benzyl-2-deoxy-D-ribofuranosides, the boronic acids 1 and 2 form the corresponding boronates preferentially with the β-anomer.