Hydrophilically augmented glycosyl carborane derivatives for incorporation in antibody conjugation reagents

Article abstract of DOI:10.1021/om00102a015

The synthesis of a series of O-glycosyl carboranes is described. The reactions of hydroxyalkyl carboranes and esterified carbohydrates, in the presence of a Lewis acid catalyst, proved to be stereoselective. Reactions of these carboranes with tri-O-acetyl-D-glucal or di-O-acetyl-D-xylal and a catalytic amount of BF₃·OEt₂ favored the formation of α anomers, while the β anomer was the major product of the SnCl₄-catalyzed reaction involving hydroxymethyl carborane and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose. The ¹H and ¹³C NMR spectra of 1-[(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)methyl]-1, 2-dicarba-closo-dodecaborane (3) were analyzed by using several one-dimensional and two-dimensional techniques; the chemical shifts and coupling interactions of all atoms were unequivocally assigned.